Which manager has won the most Champions League titles?

• Ancelotti won three titles and reached four finals with Milan and Real Madrid, and Zidane won three consecutive titles with Real Madrid
• Manchester United’s dominance in England at the time makes it surprising that it took them until 2008 to reach another final
• The UEFA Champions League is considered the most prestigious trophy in European football, which the top clubs in the continent contest

Going back-to-back in the modern era has proven beyond some of the game’s greatest coaches, while an old master in the opposing dugout could serve as inspiration.

Carlo Ancelotti has returned to Real Madrid and is attempting to establish his place in Champions League history.

Tuchel lifted ‘Ol’ Big Ears’ for the first time in last season’s 1-0 win over Manchester City in Porto. The most successful coaches since Europe’s premier competition was rebranded in 1992.

In this article, we look at the coaches with the most Champions League titles.

Carlo Ancelotti (3)

Champions League wins: 2002-03, 2006-07, 2013-14

Carlo Ancelotti has won UCL three times . Photo: MARCA

Madridistas will remember Ancelotti as the man who orchestrated La Decima, their tenth European Cup victory.

In Lisbon eight years ago, they needed a late Sergio Ramos equalizer to force extra time against Atletico Madrid before Gareth Bale, Marcelo, and Cristiano Ronaldo sealed a 4-1 win.

Before that, Ancelotti presided over finals of contrasting entertainment value, as his AC Milan won on penalties against Juventus after a dull 0-0 draw in Manchester in 2003.

 Before fumbling a 3-0 half-time lead against a Steven Gerrard-inspired Liverpool in Istanbul two years later, where they suffered their heartbreak from 12 yards.

Two years later, the Rossoneri and Ancelotti exacted their vengeance against the same opponents in Athens, with Filippo Inzaghi scoring both goals in a 2-1 victory.

Zinedine Zidane (3)

Champions League wins: 2015-16, 2016-17, 2017-18

Zinedine Zidane is the only cach who has won three UCL titles in a row. Photo: MARCA

If Ancelotti will be remembered for No. 10, it was his old assistant who made more history in Madrid.

Like his mentor, Zidane’s first success in the competition came on penalties, on Ancelotti’s old stomping ground of San Siro in 2016, with Atletico Madrid the victims again.

No one had won the European Cup since Milan won it in 1989 and 1990 under Arrigo Sacchi (Ancelotti played in both finals). Still, Madrid did so with a swaggering 4-1 victory over Juventus in Cardiff.

After accomplishing what many thoughts were impossible, Madrid defeated Liverpool 3-1 in the 2018 final, with Bale’s spectacular overhead kick highlighting their ‘threepeat’ success.

Pep Guardiola (2)

Champions League wins: 2008-09, 2010-11

Pep Guardiola has won UCL tiltes two times. Photo: Getty Images

With a decade behind him, this is the man who felt destined to top this list. Guardiola led a generation-defining Barcelona to a pair of stylish final victories over Manchester United in his first three Champions League seasons as a coach in 2009 and 2011.

The Blaugrana’s semi-final defeats to Inter and Chelsea in 2010 and 2012 set the tone for an otherwise successful Bayern Munich tenure, with the Bundesliga giants bowing out three times in a row in the final four against Spanish opposition.

Guardiola finally got over that hump with Manchester City last season, thanks to a commanding 4-1 aggregate win over Paris Saint-Germain. Still, Tuchel’s Chelsea met the newly crowned Premier League champions.

Jose Mourinho (2)

Champions League wins: 2003-04, 2009-10

Jose Mourinho has two UCL titles. Photo: Eurosport

After defeating Monaco, 3-0 in the final, Porto emerged victorious from an upset-filled and chaotic 2003-04 Champions League.

Following UEFA Cup success the previous season, Mourinho was off to the Premier League to establish himself as ‘The Special One.’

Despite being associated with England’s top flight, his spells with Chelsea, Manchester United, and Tottenham did not result in another Champions League trophy.

 His second tournament victory completed a stunning treble with Inter in 2010, which remains his crowning coaching achievement.

Sir Alex Ferguson (2)

Champions League wins: 1998-99, 2007-08

Sir Alex Ferguson won two UCL tiltes. Photo:Sports Illustrated

Manchester United never used ‘Fergie Time’ better than in 1999, when Teddy Sheringham and Ole Gunnar Solskjaer scored in injury time to defeat Bayern Munich at Camp Nou.

United’s dominance in England at the time makes it surprising that it took them until 2008 to reach another final, where John Terry’s slip in a penalty shoot-out in Moscow helped them beat Chelsea.

Ferguson intended to go back-to-back the following year, but Xavi, Andres Iniesta, Lionel Messi, and the rest got in the way, as they did two years later.

Vicente del Bosque (2)

Champions League wins: 1999-2000, 2001-02

Vicente del Bosque won UCL title two times. Photo: Skysports

In the 2001 semi-finals, Hitzfeld and Bayern defeated Real Madrid, but the trophy had a familiar home on either side.

With goals from Fernando Morientes, Steve McManaman, and Raul, Los Blancos handed compatriots Valencia their first of three consecutive final defeats in Paris.

The fact that Del Bosque’s side to Hampden Park in 2002 looked somewhat different, with the first Galacticos era in full swing, speaks volumes about Del Bosque’s adaptability and astute man-management.

And it was one of their marquee signings, Zinedine Zidane, settled the debate against Bayer Leverkusen, swivelling to volley home one of the most acceptable goals in Champions League history and secure a 2-1 win.