Challenges in the Life of Carlo Ancelotti in a Detailed Timeline

Life is full of challenges, and Carlo Ancelotti faced many. Discover key struggles and how they were overcome.

Carlo Ancelotti, nicknamed "Carletto" and "Don Carlo", is an Italian professional football manager and former player, currently managing Real Madrid. Widely considered one of the greatest managers ever, he holds the record for the most UEFA Champions League titles won (5) and is the only manager to have participated in six finals. Notably, Ancelotti is also the sole manager to have secured league titles in all of Europe's top five leagues. His accomplishments further include three FIFA Club World Cup victories and a record-setting five UEFA Super Cup wins.

Sections (5)

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

1982: Missed World Cup due to injury

In 1982, Ancelotti was very likely to be capped for the 1982 World Cup campaign, but a dramatic knee injury forced him away for several months.

1992: Forced into retirement

Despite his abilities, his playing time was cut short by several injuries, which forced Ancelotti into retirement in 1992 at the age of 33.

1997: Impeded Roberto Baggio Transfer

In 1997, Ancelotti impeded the transfer of Roberto Baggio to Parma, a decision he later regretted, stating that offensive playmakers were not compatible with his 4-4-2 system.

1997: Impeded Baggio's Transfer to Parma

In 1997, Ancelotti, then coaching Parma, impeded Roberto Baggio's transfer to the club due to his preference for a rigid 4-4-2 formation that didn't accommodate creative forwards in their preferred positions.

2005: Champions League Final Loss

In 2005, Carlo Ancelotti led Milan to the Champions League final but lost to Liverpool 2–3 on penalties after a 3–3 draw. Milan was also unable to progress beyond the quarter finals of the Coppa Italia.

2006: Serie A deduction

During the 2006-07 Serie A season, Milan received an eight-point deduction due to their role in the Calciopoli scandal.

March 2010: Champions League Elimination

On 16 March 2010, Carlo Ancelotti's Chelsea was eliminated from the Champions League after a 1–3 aggregate loss to Inter Milan.

September 2010: Chelsea lost 3-4 against Newcastle United in the League Cup

On 23 September 2010 Chelsea lost 3-4 against Newcastle United in the League Cup.

November 2010: Loss to Liverpool

On 7 November 2010, Chelsea lost to Liverpool at Anfield, 0-2.

January 2011: Defeat against Wolverhampton Wanderers

On 5 January 2011, Chelsea suffered a 0–1 defeat against Wolverhampton Wanderers, resulting in the team dropping to fifth in the league.

March 2012: First Defeat as PSG Manager

In March 2012, Ancelotti faced his first defeat as PSG manager, with the club losing 1–3 against Lyon in the Coupe de France quarter-final. PSG then suffered their first Ligue 1 defeat under Ancelotti, losing 1–2 away to Nancy.

May 2015: Dismissal from Real Madrid

In May 2015, Carlo Ancelotti was relieved of his duties as Real Madrid manager, despite having led the team to La Décima and winning the hearts of the board and fans.

September 2017: Dismissal as Bayern Munich Manager

On September 28, 2017, Carlo Ancelotti was dismissed as manager of Bayern Munich, following a 3–0 away loss to Paris Saint-Germain in the Champions League.

December 2019: Dismissal from Napoli

In December 2019, Carlo Ancelotti was dismissed as manager of Napoli, despite a 4–0 home win against Genk in the Champions League that ensured Napoli's advancement to the round of 16.

March 2020: Sent Off After Match Against Manchester United

In March 2020, Carlo Ancelotti was sent off after the full-time whistle, following an on-pitch conversation with the referee Chris Kavanagh after a controversial VAR decision against Manchester United. He was charged with misconduct by the FA the following day.

February 2021: Ancelotti's Home Burgled

In February 2021, Ancelotti's home in Crosby was burgled, with a safe being stolen and later found emptied in a nearby car park.

April 2025: Tax Evasion Trial

On April 2, 2025, Ancelotti stood trial in a Spanish court for alleged tax evasion, where he insisted his tax affairs were in order amid allegations that he failed to pay €1 million in taxes on image rights revenue.