Arsenal to Benefit From Ancelotti’s Biggest Failure in His 30-Year Coaching Career?

Arsenal to Benefit From Ancelotti’s Biggest Failure in His 30-Year Coaching Career?

  • Carlo Ancelotti is one of the most successful managers in Champions League history, having won the competition five times
  • The veteran Italian boss has one significant failure during his 30-year elite football coaching career in European soccer
  • Arsenal are in strong European form this season and could pose a serious challenge to Real Madrid in the UCL last eight

Carlo Ancelotti is one of the most respected managers the game has ever seen thanks to his five UEFA Champions League titles and multiple domestic laurels, but the experienced boss has one regret.

Despite his immense success, one glaring gap in Ancelotti's coaching career remains the fact that he has never defended a Champions League title.

Carlo Ancelotti has never won successive UEFA Champions League titles as a manager, with Arsenal vs Real Madrid UCL quarter-finals taking place on April 8
Carlo Ancelotti has never defended a UEFA Champions League title, with Arsenal vs Real Madrid UCL match taking place on April 8. Image credit: ANDY BUCHANAN/AFP and M Gracia Jimenez/Soccrates
Source: Getty Images

As Real Madrid heads into their quarterfinals clash against Arsenal, many are questioning if the Italian manager can overcome this challenge and secure back-to-back UEFA CL titles for the first time in his illustrious career that has spanned nearly 30 years.

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Ancelotti's legacy in the Champions League

Carlo Ancelotti won his first two titles with Milan in 2003 and 2007. His tactical acumen and ability to manage star-studded squads made him a revered figure at San Siro where he never lifted back-to-back UCL honours as a manager.

In the 2014 UEFA Champions League final, Ancelotti achieved his third UCL success, this time with Real Madrid, breaking a 12-year drought for the club in the competition as they clinched La Decima in Lisbon, defeating city rivals Atletico Madrid 4-1.

His mastery of European football was solidified further when he led Madrid to their 14th title in 2022, one of the most commanding victories in recent memory.

His latest triumph came in the 2024 final vs Borussia Dortmund, completing a monumental achievement that saw Ancelotti lead Madrid to yet another Champions League crown.

Despite this long list of accomplishments, defending a Champions League title has never materialised for the former PSG and Chelsea trainer.

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In each instance, the following year has seen his teams fall short, leading to questions about whether he can ever achieve consecutive triumphs in Europe’s premier competition.

Arsenal vs Real Madrid: The Gunners challenge

Ahead of the Arsenal vs Real Madrid quarter-finals first leg, the focus is on whether Ancelotti can finally break the cycle of falling short in his title defenses.

Arsenal are enjoying a period of strong form and growth in Europe this season, with in-form players like Thomas Partey who was part of the most outstanding Black Stars players in the recent international break, being tipped as men to watch in the highly-anticipated match.

Kylian Mbappe of Real Madrid celebrates with his teammates after scoring his team's third goal during the La Liga match between Real Madrid CF and CD Leganés at Estadio Santiago Bernabeu on March 29, 2025 in Madrid, Spain
Kylian Mbappe of Real Madrid celebrates with his teammates after scoring his team's third goal vs CD Leganés on March 29, 2025. Image credit: Victor Carretero/Real Madrid
Source: Getty Images

The Premier League side will take confidence from the fact that Ancelotti’s teams have often struggled to maintain their Champions League dominance the year after lifting the trophy.

A strong performance in the first leg at the Emirates on April 8 could set Arsenal up for a potentially historic upset, especially if they can exploit any weaknesses in Madrid’s lineup.

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Luck and timing

Ancelotti has often benefited from a combination of good fortune and precise decision-making during his Champions League runs. In knockout rounds, small moments can decide a tie.

If Arsenal can capitalise on these moments and keep the pressure on Real Madrid, they could force Ancelotti and his side to make mistakes. The draw certainly promises a thrilling two-legged battle between two of Europe’s most storied clubs.

Arsenal Women overpower Real Madrid Women

YEN.com.gh earlier reported on the great comeback of the Arsenal Women's team against their Real Madrid counterparts in their UEFA Women's Champions League quarter-finals this season.

The Gunners’ 3-0 victory at Emirates Stadium in Holloway overturned a 2-0 deficit from the first leg, propelling them into the semi-finals.

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Proofreading by Samuel Gitonga, copy editor at YEN.com.gh.

Source: YEN.com.gh

Authors:
Gariba Raubil avatar

Gariba Raubil (Sports Editor) Gariba Raubil is a skilled content writer and journalist with over 14 years of experience in sports journalism. He is a CAF and FIFA-accredited reporter and has been a member of the International Sports Press Association (AIPS) since 2020. He has covered several international tournaments including two All Africa Games in 2015 and 2023. He also reported on the 2017 CAF Africa Cup of Nations in Gabon and the 2018 Women’s AFCON. Email: gariba.raubil@yen.com.gh

Samuel Gitonga avatar

Samuel Gitonga (Copy editor) Samuel Gitonga is a Copy Editor at YEN.com.gh. He holds a Bachelor of Broadcast Journalism Degree from the Multimedia University of Kenya. He has over 7 years’ experience in the digital journalism industry. He started out his career at the Kenya News Agency and proceeded to work for several reputable media outlets in Nairobi.