Career Timeline of José Mourinho: Major Achievements and Milestones

From career breakthroughs to professional milestones, explore how José Mourinho made an impact.

José Mourinho, a Portuguese professional football manager currently coaching Benfica, is widely regarded as one of the most successful managers in football history. Known as "the Special One," he has won league titles in four different countries and is among the select few to have won the European Cup with two different clubs. Notably, he stands alone as the only manager to have secured victories in all three current UEFA club competitions, solidifying his legacy as a highly decorated and influential figure in the sport.

Sections (6)

Full Timeline Early Life & Education Career & Achievements Success & Recognition Challenges & Struggles Controversies & Scandals

April 1961: Biggest win in Serie A since April 1961

In April 1961, Roma achieved the biggest win in Serie A since then, thrashing Empoli 7–0 at home.

1980: Signs for Rio Ave

In 1980, Mourinho left Belenenses to sign for Rio Ave.

1981: Father joins Rio Ave

In 1981, Mourinho was joined at Rio Ave by his father, who was named first team manager.

1991: Roma reaches first European final since 1991

On 5 May, José Mourinho guided Roma to their first European final since 1991 by beating Leicester City 2–1 on aggregate in the semi-finals of the Europa Conference League.

1992: Translator for Bobby Robson

In 1992, Mourinho became a translator for Bobby Robson at Sporting CP.

December 1993: Robson sacked

In December 1993, Bobby Robson was sacked by Sporting CP.

1994: Taça de Portugal win

In 1994, Porto, with Robson and Mourinho, won the Taça de Portugal.

1995: Portuguese Championship win

In 1995, Porto, with Robson and Mourinho, won the Portuguese championship.

1996: Joins Barcelona

In 1996, Mourinho joined Barcelona with Bobby Robson.

1996: Portuguese Championship win

In 1996, Porto, with Robson and Mourinho, won the Portuguese championship and the Portuguese Super Cup.

September 2000: Appointed Benfica manager

In September 2000, Mourinho was appointed as the manager for Benfica.

December 2000: Resigns from Benfica

In December 2000, Mourinho resigned from his position as manager of Benfica after just nine league games in charge.

2000: Copa Catalunya win

In 2000, Barcelona, under Mourinho, won the Copa Catalunya.

July 2001: Managerial Post with União de Leiria

In July 2001, Mourinho secured a new managerial position with União de Leiria.

November 2001: União de Leiria recording eight matches unbeaten

In November 2001, Mourinho recorded eight matches unbeaten in the league since November 25, 2001.

January 2002: Mourinho replaces Octávio Machado at Porto

In January 2002, José Mourinho was chosen to replace Octávio Machado as the manager of Porto. At the time, Porto was fifth in the Liga and had been eliminated from other competitions. Mourinho guided them to third place that year.

January 2002: União de Leiria draws against Santa Clara

On January 20, 2002, União de Leiria drew 1-1 against Santa Clara. Mourinho recorded eight matches unbeaten in the league since November 25, 2001.

2002: Returns to Porto and wins Primeira Liga titles

In 2002, José Mourinho returned to Porto, where he won two Primeira Liga titles, the Taça de Portugal, the UEFA Cup, and the UEFA Champions League.

2002: End of trophy-less streak for Mourinho

In April 2021, José Mourinho's sacking by Tottenham Hotspur marked the first time since 2002 that Mourinho had departed a club without winning a trophy.

May 2003: Porto wins Taça de Portugal and UEFA Cup

In May 2003, José Mourinho's Porto won the Taça de Portugal, beating Leiria in the final, and also won the UEFA Cup final against Celtic.

2003: Reaching back-to-back European finals

In 2003, José Mourinho reached back-to-back European finals, repeating a feat he had previously achieved during his time at Porto.

May 2004: Porto loses Taça de Portugal Final but wins UEFA Champions League

In May 2004, Porto lost the Taça de Portugal Final to Benfica. However, two weeks later, the team won the UEFA Champions League by defeating Monaco 3–0 in Germany.

June 2004: Mourinho moves to Chelsea

In June 2004, José Mourinho moved to Chelsea on a three-year contract, becoming the first Portuguese manager in the Premier League. At a press conference, he described himself as a "top manager".

2004: Origin of "Park the Bus" Phrase

In 2004, José Mourinho coined the phrase "park the bus" to describe Tottenham Hotspur's defensive tactics during a 0-0 draw against his Chelsea side, which eventually made it to the Oxford English Dictionary in 2022.

2004: Reaching back-to-back European finals

In 2004, José Mourinho reached back-to-back European finals, repeating a feat he had previously achieved during his time at Porto.

2004: Mourinho joins Chelsea

In 2004, Mourinho joined Chelsea, announcing himself as "the Special One" at his first press conference.

2004: Champions League Knockout Stage Game

In 2004, during a Champions League knockout stage game between Porto and Manchester United, José Mourinho targeted United's weaknesses on the flanks, especially on the left where Quinton Fortune was protected by Ryan Giggs.

2004: Champions League Celebration at Old Trafford

In 2004, during the Champions League round of 16 against Manchester United, José Mourinho had an iconic celebration at Old Trafford after his team won. He later recalled it when questioned about his celebration against Siena in 2008.

2004: Mourinho References His First Promises to Chelsea

In June 2013, upon being appointed as Chelsea manager for the second time, Mourinho referenced the promises he made in 2004 during his initial appointment.

2004: Self Proclamation

Since the self proclamation in 2004, Mourinho is often nicknamed "The Special One".

2005: Chelsea wins Premier League title, Mourinho throws medal into crowd

In 2005, Chelsea defeated Arsenal to win the FA Community Shield and also topped the Premier League. Chelsea beat Manchester United to win their second consecutive Premier League title. After the presentation, José Mourinho threw Robert Huth's championship medal into the crowd.

2005: Referencing the 2005 Serie A Title

In January 2009, José Mourinho made controversial comments about Inter's past Serie A titles, referencing the controversial 2005–06 Serie A title awarded to third-placed Inter in the aftermath of the Calciopoli scandal.

2006: Tactical Switch at Chelsea

In 2006, Andrei Shevchenko's signing led José Mourinho to switch to a 4–1–3–2 formation at Chelsea.

2006: Media speculates Mourinho will leave Chelsea

In 2006, there was media speculation that José Mourinho would leave Chelsea due to poor relations with Roman Abramovich. Mourinho cleared doubts, stating he would only leave if Chelsea didn't offer him a new contract by June 2010, or if he was sacked.

May 2007: Chelsea wins FA Cup Final against Manchester United

In May 2007, José Mourinho led Chelsea to a 1–0 victory against Manchester United in the FA Cup Final, the first final played at the rebuilt Wembley. This was his first FA Cup win, meaning he had won every domestic trophy available to a Premier League manager.

September 2007: Mourinho unexpectedly leaves Chelsea

In September 2007, José Mourinho unexpectedly left Chelsea "by mutual consent" after a series of disagreements with owner Roman Abramovich. He left as the most successful manager in Chelsea's history.

2007: Departure from Chelsea

In 2007, Mourinho departed from Chelsea after three seasons amid reports of disagreements with owner Roman Abramovich.

June 2008: Mourinho Appointed Inter Milan Manager

In June 2008, José Mourinho was appointed the successor of Roberto Mancini at Inter Milan on a three-year contract. He brought along much of his backroom staff and chose Giuseppe Baresi as his assistant.

December 2008: Celebration and Controversy After Siena Match

In December 2008, after Inter's victory against Siena, José Mourinho's exuberant celebration in front of Inter supporters led to criticism from journalist Maurizio Pistocchi, who deemed it disrespectful to Siena fans. Mourinho defended his actions, referencing a similar celebration at Old Trafford in 2004.

2008: Joins Inter Milan

In 2008, Mourinho joined Italian club Inter Milan as manager.

January 2009: Controversial Halftime Comments

During halftime of a January 2009 match against Atalanta, José Mourinho made controversial comments about Inter's past Serie A titles, calling them a "shitty team." He later admitted to making the statement, justifying it as a motivational tactic.

March 2009: Press Conference Accusations

In March 2009, during a press conference, José Mourinho asserted that Milan and Roma would not win any honors that season. He also accused Juventus of benefiting from referee mistakes and criticized Italian sports journalists for "intellectual prostitution".

April 2009: Adriano Leaves Inter

In April 2009, Adriano left Inter. The exit of the Brazilian striker was followed by the Argentine duo Julio Cruz and Hernán Crespo. Legendary Portuguese attacking midfielder and veteran Luís Figo retired.

May 2009: Inter Mathematically Wins Serie A Title

In May 2009, Inter Milan mathematically won the Serie A title after runners-up Milan lost to Udinese, leaving Inter seven points above their rivals with only two games remaining.

July 2009: Mourinho Expresses Interest in Manchester United Job

In July 2009, José Mourinho was reported to have shown interest in taking over at Manchester United when Alex Ferguson retired, stating he would consider it if United wanted him as Ferguson's successor.

December 2009: Altercation with Journalist Andrea Ramazzotti

In December 2009, following a draw with Atalanta, José Mourinho allegedly insulted and grabbed Corriere della Sera journalist Andrea Ramazzotti, who had permission to be near the Inter bus. This led to widespread condemnation and an apology from Inter's president, Massimo Moratti. Mourinho was also referred to the Federal Prosecutor.

2009: Defeat against Barcelona

In 2009, During the second leg of the Champions League semi-final against Barcelona, Motta’s sending off led Mourinho to sit deep and narrow to defend their lead from the first leg away from home, while Barcelona were allowed possession.

2009: Pundit praises Mourinho

In 2009, Pundit Nicky Bandini praised Mourinho for his ability to motivate his players and a create a united team environment during Inter's 2009–10 treble winning season

2009: Real Madrid's Underperformance and Alcorconazo

In 2009, Real Madrid, despite having star players, underperformed and suffered a shocking defeat to Alcorcón in the Copa del Rey. This period was marked by significant disappointment.

2009: Argument with Marcello Lippi

In the summer of 2009, José Mourinho had an argument with Italy's national team coach, Marcello Lippi, after Lippi predicted Juventus would win the Serie A title in the 2009-10 season. Mourinho viewed this as disrespectful to Inter.

2009: Inter Milan's UEFA Champions League win

On 24 May, 2022 José Mourinho won his first title with Roma, marking the first time a Serie A team won a continental championship since Inter Milan's 2009–10 UEFA Champions League, achieved under Mourinho himself as coach.

February 2010: Handcuffs Gesture and Referee Criticism

During a Serie A game against Sampdoria in February 2010, José Mourinho made a handcuffs gesture towards a camera to protest the refereeing, resulting in a three-game ban. He further complained about a denied penalty and the booking of Samuel Eto'o for diving, which led to a show of support from the San Siro crowd.

February 2010: Responses to Criticism from Other Managers

In February 2010, José Mourinho responded through his spokesman, Eladio Parames, to criticisms from Juventus manager Claudio Ranieri and Napoli manager Walter Mazzarri after controversial refereeing decisions and a press blackout imposed by Moratti.

February 2010: Defense of Inter's Performances and Criticism of Other Managers

In February 2010, after two draws, José Mourinho defended Inter's performances and criticized Napoli's manager, Walter Mazzarri, and president, Aurelio De Laurentiis, using sharp words.

April 2010: Inter Reaches Champions League Semi-Finals and Coppa Italia Final

In April 2010, José Mourinho became the first manager in history to take three teams to the semi-finals of the Champions League. Inter overcame CSKA Moscow in the quarter-finals. Inter also reached the Coppa Italia final, for the first time under Mourinho, with a victory over Fiorentina.

April 2010: Mourinho Reaches Champions League Final with Inter

In April 2010, José Mourinho reached the Champions League final for the second time in his career after Inter beat holders Barcelona. The match ended 3-2 on aggregate, despite losing 1-0 at Camp Nou. Mourinho had a confrontation with Barcelona's goalkeeper after the match.

May 2010: Inter Wins Serie A, Coppa Italia, and Champions League

In May 2010, Inter secured the Serie A title after a win against Lazio, won the Coppa Italia by defeating Roma, and then won the Champions League against Bayern Munich. Inter became the first Italian club to complete the treble.

May 2010: Mourinho Becomes Real Madrid Manager

In May 2010, José Mourinho took over from Manuel Pellegrini at Real Madrid, signing a four-year contract. He was appointed sporting manager and first-team coach.

May 2010: Mourinho Announces Departure from Inter

In May 2010, the day after winning the Champions League, José Mourinho announced he was likely leaving Inter. Days later, a compensation package was agreed with Real Madrid, and he was released by Inter.

June 2010: Mourinho's contract expiry mentioned

In June 2010, José Mourinho indicated that his contract with Chelsea was expiring, and that he would only leave if Chelsea didn't offer him a new contract before its expiry.

August 2010: Mourinho's First La Liga Game and Subsequent Victories

On August 29, 2010, Mourinho's first La Liga game as manager of Real Madrid resulted in a 0–0 draw at Mallorca. He predicted that a rival team would soon "pay for the chances we've missed today", a statement which was confirmed as Real Madrid went on to defeat Deportivo de La Coruña, Málaga, and Racing Santander.

November 2010: UEFA Investigation and Sanctions for Improper Conduct

In November 2010, during a Champions League match against Ajax, Real Madrid players received late second yellow cards for time-wasting, leading to a UEFA investigation. José Mourinho was charged with improper conduct, fined £33,500, and given a one-match Champions League ban for allegedly instructing the players.

December 2010: Widest Margin Victory Against Levante

On December 22, 2010, Mourinho achieved the widest margin victory in his career, winning 8-0 against Levante in the first leg of their Copa del Rey quarter-final.

2010: Real Madrid Manager

In 2010, José Mourinho became the manager of Real Madrid, utilizing a 4–2–3–1 formation.

2010: Continental treble with Inter Milan

In 2010, Mourinho led Inter Milan to a continental treble, winning Serie A, the Coppa Italia, and the UEFA Champions League.

2010: Pep Guardiola praises Mourinho

In 2010, Pep Guardiola described José Mourinho as "probably the best coach in the world".

2010: New Players and La Liga Performance

In 2010, Real Madrid finished second in La Liga with a club record of 96 points, despite an elimination from the Champions League. Following the 2010 FIFA World Cup, Mourinho brought in Sami Khedira, Mesut Özil, Ricardo Carvalho, and Ángel Di María to the team.

April 2011: Copa del Rey Victory and Champions League Semi-Finals

On April 20, 2011, Mourinho won his first trophy in Spanish football, the Copa del Rey, defeating Barcelona 1-0. Later that month, Real Madrid was eliminated from the Champions League semi-finals after facing Barcelona.

August 2011: Eye-Gouging Incident in Supercopa de España

On August 17, 2011, during the Supercopa de España final, José Mourinho was seen gouging the eye of Barcelona's assistant coach Tito Vilanova during a brawl. After the game, Mourinho claimed he did not know who "Pito" Vilanova was.

December 2011: Real Madrid Completes Champions League Group Stage with Six Victories

On December 7, 2011, Real Madrid defeated Ajax 3-0, completing the Champions League group stage with six victories, matching a club record set 50 years earlier in 1961.

2011: La Liga title with Real Madrid

In 2011, Mourinho's Real Madrid broke several domestic records for points, goals scored, and wins in a season and won La Liga.

2011: Counter-attacking system at Real Madrid

In the 2011-12 season, José Mourinho's Real Madrid team implemented a counter-attacking system, which led to breaking records, including 100 points and 121 goals.

April 2012: Real Madrid Wins El Clásico, Extends La Liga Lead

On April 21, 2012, Real Madrid defeated Barcelona in El Clásico, extending their lead in La Liga to seven points. This was their first La Liga victory against Barcelona since 2008 and broke the record for most goals scored in the championship.

May 2012: Real Madrid Clinches La Liga Title

In May 2012, Real Madrid won the Liga title for the first time in four years. They set records for most games won in a La Liga season (32), most away wins (16), and most points obtained in any of the top European leagues (100).

May 2012: Mourinho Signs New Four-Year Contract and Wins Supercopa de España

On May 22, 2012, Mourinho signed a new four-year contract with Real Madrid. He won the Supercopa de España, becoming the only coach to win the national super cups in four European countries and the first manager to win every domestic title in four European leagues.

2012: Mourinho Signed a Contract Extension

In 2012, Mourinho had signed a contract extension, to 2016, but left the club by "mutual agreement" a year later.

2012: Tactical change against Manchester United

In 2012, during a Champions League match against Manchester United, José Mourinho quickly introduced Luka Modrić after Nani's dismissal, leading to two quick goals and turning the game in Real Madrid's favour.

June 2013: Mourinho Appointed Chelsea Manager for Second Time

In June 2013, Chelsea appointed Mourinho as manager for the second time, on a four-year contract. He expressed his passion for Chelsea and promised to be "one of them."

August 2013: Return to Chelsea and UEFA Super Cup Loss

In August 2013, Mourinho's first competitive game back at Chelsea was a 2-0 victory against Hull City. Chelsea then lost the UEFA Super Cup to Bayern Munich on penalties, despite leading.

2013: End of Real Madrid Tenure

By 2013, after three seasons, José Mourinho consistently led Real Madrid to the semi-finals of the Champions League.

2013: Chelsea's Season

During the 2013–14 season, Mourinho consistently played down Chelsea's title chances and referred to it as a transitional season. Chelsea went on to finish third in the 2013–14 Premier League, four points behind champions Manchester City, and was eliminated in the semi-finals of the 2013–14 Champions League by Atlético Madrid.

2013: Champions League knockout game

In 2013, during a Champions League knockout game against Paris Saint-Germain, José Mourinho played a risky 4–1–2–3 in the last quarter, which led to Demba Ba's winning goal.

2013: Worst Season and Departure from Real Madrid

In 2013, following the Copa del Rey final loss on May 17, Mourinho called the 2012-13 season "the worst of my career." On May 20, Real Madrid announced Mourinho would leave the club at the end of the season by mutual agreement.

April 2014: First Home League Defeat and Transitional Season

On April 19, 2014, Mourinho suffered his first home league defeat as Chelsea manager in a 2-1 loss to Sunderland. He referred to the season as transitional and dropped Juan Mata. Chelsea finished third in the Premier League and was eliminated in the Champions League semi-finals.

2014: Chelsea's Premier League Campaign Start

In 2014, Chelsea started their Premier League campaign with a 3-1 victory against Burnley. This match marked the first competitive action for new signings Diego Costa, Cesc Fàbregas and Thibaut Courtois. Didier Drogba made his return appearance to the Chelsea squad.

2014: Global Ambassador of the United Nations' World Food Programme

Since his appointment in 2014, Mourinho acts as a Global Ambassador of the United Nations' World Food Programme.

March 2015: League Cup Victory and Champions League Exit

In March 2015, Chelsea defeated Tottenham Hotspur to win the League Cup, Mourinho's first trophy since returning to Chelsea. However, they were knocked out of the Champions League by Paris Saint-Germain.

May 2015: Chelsea Crowned Premier League Champions

In May 2015, Chelsea were crowned Premier League champions, losing only three matches. Mourinho was named Premier League Manager of the Season.

August 2015: New Contract and 100th Home Match

In August 2015, Mourinho signed a new four-year contract with Chelsea. He reached his 100th Premier League home match, which ended in a loss to Crystal Palace. Chelsea had a poor start to the season and was eliminated from the League Cup.

December 2015: Departure from Chelsea

In December 2015, after losing nine of 16 Premier League matches, Chelsea announced that they had parted company with Mourinho by mutual consent.

2015: Dismissed from Chelsea

In 2015, Mourinho was dismissed from Chelsea after a poor run of results.

May 2016: Mourinho Signs with Manchester United

On May 27, 2016, Mourinho signed a three-year contract with Manchester United, with an option to stay until at least 2020.

August 2016: Community Shield Victory and First Premier League Game

On August 7, 2016, Mourinho won his first trophy with Manchester United, the FA Community Shield, beating Leicester City. He was victorious in his first Premier League game as United boss on August 14.

October 2016: Return to Chelsea and EFL Cup Victory

In October 2016, Mourinho returned to Chelsea with Manchester United, resulting in a 4-0 defeat. Later that month, he won his second Manchester derby in the EFL Cup.

October 2016: Alleged Humiliation Accusation Against Antonio Conte

On October 23, 2016, while Manchester United trailed Chelsea 4-0, José Mourinho reportedly accused Chelsea manager Antonio Conte of trying to humiliate United with his actions. This was revealed after Mourinho whispered something into Conte's ear after the match, but neither confirmed the reports.

2016: Appointed manager of Manchester United

In 2016, Mourinho was appointed manager of Manchester United.

2016: Mourinho's Contract Extension

Mourinho had a contract extension to 2016, but left the club by "mutual agreement" in 2013.

2016: Contract Extension Until 2016

On May 22, 2012, Mourinho signed a new four-year contract to remain as Real Madrid manager through to 2016.

January 2017: Manchester United reach EFL Cup Final

On 29 January 2017, despite a 2–1 second leg loss away to Hull City, José Mourinho's Manchester United reached the final of the EFL Cup by virtue of a 3–2 aggregate win.

February 2017: Roma wins against Inter

On 1 October, 2022 Roma recorded their first win against Inter since February 2017.

April 2017: Manchester United beat league leaders Chelsea

In April 2017, José Mourinho's Manchester United beat league leaders Chelsea 2–0, with Ander Herrera man-marking Eden Hazard.

May 2017: Manchester United win Europa League

On 24 May 2017, Manchester United won the Europa League courtesy of a 2–0 win over Ajax, marking José Mourinho's second major trophy in his first season as Manchester United manager and maintaining his 100% record of winning every major European Cup final as a manager.

2017: Manchester United's summer signings and season start

In the summer of 2017, José Mourinho strengthened his Manchester United side with the signings of Romelu Lukaku, Victor Lindelöf, and Nemanja Matić, and Manchester United made a strong start to the season.

January 2018: Conte calls Mourinho "a little man"

In January 2018, the feud between Mourinho and Conte intensified, with Conte calling Mourinho "a little man" amidst continued verbal sparring.

March 2018: "Football Heritage" Speech

On March 16, 2018, following Manchester United's loss to Sevilla in the UEFA Champions League, José Mourinho delivered the "Football Heritage" speech. He criticized the management of Manchester United, implying success depends on player quality.

October 2018: Mourinho involved in tunnel incident at Chelsea game

On 20 October 2018, José Mourinho was involved in a tunnel incident at a Manchester United game against his former club Chelsea, following a provocative celebration by a Chelsea coach after a late equaliser. Mourinho also reminded Chelsea fans of his three Premier League titles won for the club.

December 2018: Mourinho sacked by Manchester United

On 18 December 2018, José Mourinho was sacked by Manchester United after a poor start to the 2018–19 season, which left the club 19 points behind the league leaders.

2018: Analyst for RT at the 2018 FIFA World Cup

In 2018, José Mourinho became an analyst for RT to cover the 2018 FIFA World Cup.

2018: Manchester United's season and FA Cup Final loss

In 2018, José Mourinho faced criticism for Manchester United's Champions League exit to Sevilla, defended his United career in a rant, finished second in the Premier League, and lost the FA Cup Final to Chelsea.

2018: Mourinho demands respect after loss to Tottenham Hotspur

In 2018, after a 3-0 home loss to Tottenham Hotspur, José Mourinho demanded respect from journalists, citing his Premier League trophy wins and asserting his status as one of the greatest managers in the world.

August 2019: Joins Sky Sports as a Pundit

In August 2019, José Mourinho joined UK broadcaster Sky Sports as a pundit on their Premier League coverage.

November 2019: Mourinho's first match and comments on ball boy

In November 2019, José Mourinho managed his first match with Tottenham Hotspur in a 3–2 away win against West Ham United on 23rd. On 26th, he sparked media attention by claiming that ball boy Callum Hynes 'assisted' Spurs' second goal in a 4–2 win over Olympiacos in the Champions League.

November 2019: Mourinho appointed manager of Tottenham Hotspur

On 20 November 2019, José Mourinho was appointed as the manager of Tottenham Hotspur on a four-year contract, replacing Mauricio Pochettino.

2019: Appearance in DAZN's "The Making Of" series

In 2019, José Mourinho collaborated with DAZN, appearing in "The Making Of" series, a documentary that relives significant games defining football icons.

2019: Appointed manager of Tottenham Hotspur

In 2019, Mourinho was appointed manager of Tottenham Hotspur.

2019: Mourinho's Contract

In August 2015, Mourinho signed a new four-year contract with Chelsea that would have kept him at Stamford Bridge until 2019.

June 2020: Mourinho records 300th win in English football

On 23 June 2020, José Mourinho recorded his 300th win in English football when Tottenham beat West Ham United 2–0.

July 2020: Mourinho secures first win at St James' Park

On 15 July 2020, José Mourinho secured his first ever win as a manager at St James' Park when Tottenham defeated Newcastle by a scoreline of 3–1.

October 2020: Tottenham Hotspur win against Manchester United

On 4 October 2020, José Mourinho managed Tottenham Hotspur to a 6–1 win against his former club Manchester United at Old Trafford.

December 2020: Tottenham on top of Premier League

On 6 December 2020, A 2–0 victory over Arsenal put Tottenham on top of the Premier League and meant José Mourinho was only the club's second manager to win his first two North London derbies.

2020: Involvement in "All or Nothing: Tottenham Hotspur"

In 2020, José Mourinho was involved in the Amazon Prime sports docuseries "All or Nothing: Tottenham Hotspur" during his management spell, adding to his media appearances.

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2020: Option to Stay at the Club Until At Least 2020

In May 2016, Mourinho signed a three-year contract with Manchester United, with an option to stay at the club until at least 2020.

2020: Tottenham eliminated from the UEFA Europa League

On 18 March, 2021 Tottenham lost 3–0 to Dinamo Zagreb after extra time in the second leg of the 2020–21 UEFA Europa League round of 16, being eliminated from the competition 3–2 on aggregate.

February 2021: Tottenham knocked out of the FA Cup and lose to Chelsea

In February 2021, Tottenham were knocked out of the FA Cup, losing 5–4 after extra time to Everton on 10th. On 23rd, Tottenham lost 1–0 to Chelsea, marking the first time in José Mourinho's career that he had lost two consecutive home games.

April 2021: Mourinho sacked by Tottenham Hotspur

On 19 April 2021, José Mourinho was sacked by Tottenham Hotspur after 17 months in charge of the club, days before the EFL Cup Final against Manchester City.

May 2021: Mourinho appointed head coach of Roma

On 4 May 2021, José Mourinho was appointed head coach of Roma from the start of the 2021–22 season, replacing Paulo Fonseca.

August 2021: Mourinho manages first match with Roma and returns to Serie A

In August 2021, José Mourinho managed his first match with Roma in a 2–1 away win against Trabzonspor in the first leg of the UEFA Europa Conference League play-off round on 19th. On 22nd, he made his return to Serie A, after eleven years, managing a 3–1 home victory over Fiorentina at Stadio Olimpico. On 26th, Mourinho secured qualification for the Europa Conference League, after overseeing a 3–0 home win against Trabzonspor in the play-off second leg.

September 2021: Mourinho reaches 1,000 games as a manager and loses Roma derby

In September 2021, José Mourinho reached 1,000 games as a manager in a 2–1 win against Sassuolo on 12th. On 26th, against Lazio, Roma lost 2–3, and Mourinho became the first Roma manager to lose his first Serie A Roma's derby since Luis Enrique in 2011.

September 2021: Blaming VAR and Referee After Loss to Lazio

On September 26, 2021, following a loss to Lazio, José Mourinho criticized the VAR and the referee for the result, sparking controversy.

2021: Managed Roma

In 2021, José Mourinho managed Roma.

February 2022: Red Card and Ban After Incident Against Hellas Verona

In February 2022, during a match against Hellas Verona, José Mourinho was red-carded for kicking the ball and making a telephone gesture toward the referee, reportedly saying "Juventus sent you". He received a two-match touchline ban and a €20,000 fine.

March 2022: Mourinho wins first Derby della Capitale with Roma

On 20 March 2022, José Mourinho won his first Derby della Capitale after managing a 3–0 win over Lazio.

August 2022: Roma began their league season with a 1-0 away win.

In August 2022, Roma began their league season with a 1–0 away win over Salernitana on 14th.

October 2022: "Park the bus" Added to Oxford English Dictionary

In October 2022, José Mourinho's phrase "park the bus" was added to the Oxford English Dictionary, acknowledging its cultural impact on football terminology.

2022: Roma's transfer window

In José Mourinho's second transfer window at Roma to prepare for the 2022–23 season, the club signed several players, including Paulo Dybala.

2022: Roma wins UEFA Europa Conference League Final

On 24 May, 2022 José Mourinho won his first title with Roma by defeating Feyenoord in the 2022 UEFA Europa Conference League Final. This was Roma's first trophy in 11 years, making him the third manager – after Udo Lattek and Giovanni Trapattoni – to have won all three existing major European trophies.

February 2023: Roma knocked out of the Coppa Italia

On 1 February 2023, Roma were knocked out of the Coppa Italia, losing 2–1 at home to Cremonese. On 28 February, Roma was beaten again by Cremonese, the latter's first win in Serie A in 27 years.

February 2023: Red Card Against Cremonese

On February 28, 2023, José Mourinho received a red card during a match against Cremonese. He claimed he was provoked by the fourth official. He received a two-game ban and was fined 10,000 euros for the incident.

2023: Consecutive losses against Lazio and AC Milan

In 2023, Roma experienced two consecutive losses against Lazio in the Coppa Italia quarter-finals and against AC Milan in the league, contributing to Mourinho's departure in January 2024.

January 2024: Parting ways with Roma

On January 16, 2024, Roma announced that they parted ways with José Mourinho with immediate effect, following a negative string of results.

June 2024: New manager of Fenerbahçe

On June 2, 2024, José Mourinho was officially unveiled as the new manager of Turkish side Fenerbahçe and presented to the fans.

July 2024: Joined Fenerbahçe

In July 2024, José Mourinho joined Turkish Süper Lig club Fenerbahçe.

November 2024: Suspension for Comments About Süper Lig

On November 8, 2024, José Mourinho received a one-game suspension for comments made at a press conference regarding the Süper Lig. He was critical of the league's quality and refereeing.

February 2025: Criminal Proceedings Initiated After Galatasaray Draw

On February 25, 2025, after a draw against Galatasaray, Galatasaray initiated criminal proceedings against José Mourinho for comments they claimed were racist. Mourinho praised the Slovenian referee and criticized Turkish referees, leading to a suspension and fine, which had been later cut.