Challenges in the Life of José Mourinho in a Detailed Timeline

By Popular Timelines Editorial Team · Updated: May 2, 2026

A closer look at the defining struggles that shaped José Mourinho's life and career.

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

December 2000: Resigns from Benfica

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

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 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.

March 2005: Accusations of referee bias

In March 2005, following a Champions League tie between Chelsea and Barcelona, José Mourinho accused referee Anders Frisk and Barcelona coach Frank Rijkaard of breaking FIFA rules, leading to a touchline ban.

June 2005: Fine for meeting with Ashley Cole

On June 2, 2005, José Mourinho was initially fined £200,000 for his part in the meeting with then Arsenal full-back Ashley Cole in January of that year, but the fine was reduced to £75,000 after a hearing in August.

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.

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.

2007: Friction between Mourinho and Abramovich over Avram Grant appointment

In 2007, there was friction between José Mourinho and Roman Abramovich when Avram Grant was appointed as director of football despite Mourinho's objections.

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.

November 2010: Mourinho's First El Clásico Defeat

On November 29, 2010, Mourinho's Real Madrid was defeated in his first El Clásico encounter against Barcelona, with a score of 5-0. Florentino Pérez regarded it as the worst game in the history of Real Madrid. Mourinho refused to call the loss a humiliation.

2011: Accusations of defensive play

In 2011, Morten Olsen concluded that he doesn't "like his persona or the way he plays football negatively".

2012: Hint of Departure and Growing Tensions

In 2012, After the second leg with Dortmund, Mourinho hinted that the 2012–13 season with Real Madrid would be his last, citing love from other clubs and hatred from some individuals in Spain. There were growing tensions between fans, players and Real Madrid officials.

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: Tensions Within Real Madrid

In 2013, Mourinho's relationships with Sergio Ramos and Iker Casillas caused divisions between fans. His relationship with Cristiano Ronaldo became difficult due to differing opinions on the player's improvement. Mourinho faced criticism for controversial incidents.

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.

January 2015: FA Cup Elimination

In January 2015, Chelsea were knocked out of the FA Cup fourth round by Bradford City, which Mourinho described as a "disgrace".

2015: Dismissed from Chelsea

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

September 2016: First Manchester Derby Loss

On September 11, 2016, Mourinho lost his first Manchester derby as a manager to Manchester City, marking his eighth loss against Pep Guardiola.

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: 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.

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.

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.

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.