With which clubs have Pep Guardiola and Carlo Ancelotti won the Champions League?

Of the coaches left in this season’s Champions League, three know what it’s like to win the trophy – and two of them, Pep Guardiola and Carlo Ancelotti have managed it multiple times. Both have ended on the losing side too – Guardiola’s City reached the final for the first time last year only to lose to Premier League rivals Chelsea.

Of the four, Ancelotti has the most titles – he will be looking to lift Ol’ Big Ears for the fourth time. He is one of only a handful of coaches who have been crowned European champions with two different clubs – and shares the record for the most triumphs in history - three, a record he shares with Bob Paisley (Liverpool – 1976/7, 1977/8 and 1980/1) and Zinedine Zidane (Real Madrid - 2015/16, 2016/17 and 2017/18).

Ancelotti’s first Champions League with AC Milan

As a player, Ancelotti won the old European Cup twice with the legendary AC Milan side of the late 1980s. His first Champions League as a coach arrived in 2002/3 – the final itself, an all-Italian affair between his Milan and Juventus wasn’t exactly a classic. It ended without goals at Old Trafford and was decided from the penalty spot, Ancelotti’s team prevailing 2-3 in the shootout.

As a spectacle, his next final was much more entertaining. Paolo Maldini and Hernán Crespo had given Ancelotti’s Milan a seemingly unassailable three-goal lead in the first 45 minutes in Istanbul in 2004/5. But Liverpool miraculously clawed their way back, levelling the score in a frenzied, seven minute spell after the break, to take the final into extra-time, then penalties in one of the most remarkable comebacks in European club football history.

A couple of seasons later, Ancelotti got his revenge against the same rivals to pick up his second Champions League with Milan. Goals in each half from Pippo Inzaghi set Milan on their way and there was no comeback this time from Liverpool, who pulled a late consolation goal back from Dirk Kuyt. It ended 2-1 for Ancelotti to claim the second European crown of his managerial career.

Carlo’s third title was arguably his most memorable. He guided Real Madrid to their long-awaited 10th title, La Décima in Lisbon. Madrid faced city rivals Atlético in the 2013/14 Champions League final – the first final to be played between clubs from the same city. In terms of drama, it was on a par with the 2005 final – Ancelotti’s team spent most of the match trailing, Atleti had stubbornly held their ground after Diego Godín had put them ahead on 36 minutes. But with the clock ticking down, Sergio Ramos headed Madrid back level deep into stoppage-time. Los Blancos made short work of extra-time, with Gareth Bale, Marcelo and Cristiano Ronaldo adding another three goals to put the game beyond their neighbours. Madrid had at last won La Décima, and Ancelotti his third Champions League title – two with Milan and one with Real Madrid.

Guardiola, success with Barcelona, semi-final disappointments with Bayern

Guardiola has had several stabs at winning the Champions League since clinching his first one with Barcelona in 2008/9. That Barça side had already won the Copa del Rey and LaLiga that year before being proclaimed European champions, beating Manchester United 2-0 at the Olimpico in Rome in to become the first Spanish club to complete the treble. Not bad for his first season in charge.

Pep’s second Champions League came two years later in 2010/11 – his Barcelona team faced Man United in the final for the second time. It ended 3-1 at Wembley with Pedro, Messi and David Villa finding the target for the Catalans and Wayne Rooney grabbing United’s only goal of the game.

Guardiola left Barça in 2013 to join Bundesliga giants and cup holders Bayern Munich, who had lifted the trophy months earlier under Jupp Heynckes. Pep spent three seasons in Germany, with the goal of leading Bayern to their sixth title but he fell short of achieving that. The team were eliminated at the semi-final stage by Real Madrid in his first season, then denied a place in the following year’s final by his old club, Barcelona. Guardiola’s Bayern reached the semis for the third year running in 2015/16 only to be knocked out by Spanish opposition again – losing to Atlético Madrid on the away goals rule after it finished 2-2 on aggregate.