Saturday’s Champions League final will pit Carlo Ancelotti against an English side in Europe for the 26th time.
As manager of Juventus, Milan, Chelsea, Real Madrid, Napoli and Bayern Munich, he has faced several sides from England across both the Champions League and Europa League.
Here, we take a look at his record…
Champions League semi-final, 1999: JUVENTUS vs. Manchester United
The first meeting between Ancelotti and Sir Alex Ferguson and Juve were unlucky to leave Old Trafford with just a draw in the first leg having led for the most of the match.
But the return produced a Champions League classic as United came from 2-0 down to win 3-2 and end Juve’s run consecutive finals at three.
Champions League last-16, 2005: MILAN vs. Manchester United
By their second meeting, both Ancelotti and Ferguson were Champions League-winning managers but the Rossoneri were a level above on this occasions.
Hernan Crespo scored twice as Milan won 1-0 in both legs.
Champions League final, 2005: MILAN vs. Liverpool
One of the lowest points of Ancelotti’s managerial career. Heavy favourites coming into the match, Milan raced to a 3-0 lead at half-time.
But by the hour mark, Liverpool were level. Milan dominated extra time but couldn’t find a way through and were beaten on penalties.
Champions League semi-final, 2007: MILAN vs. Manchester United
Ancelotti’s Milan were the top side in Europe at this point but, despite Kaka’s super show, United came from behind to win 3-2 in the first leg at Old Trafford.
But the return is arguably the finest performance by an Ancelotti side as the Rossoneri battered United 3-0 under the Milan rain.
Champions League final, 2007: MILAN vs. Liverpool
Revenge for Milan as Filippo Inzaghi’s double set the Rossoneri up for a 2-1 win in Athens.
Liverpool pulled one back to set up a tense finish but it was Champions League No. 2 for Ancelotti.
Champions League last-16, 2008: MILAN vs. Arsenal
The great Milan side was on its way down here. Despite being the holders, they fell at the first knockout stage.
A 0-0 draw in London was not enough for the Rossoneri, who were beaten 2-0 at San Siro.
Europa League group stage, 2008: MILAN vs. Portsmouth
A fifth-place finish in Serie A had condemned the Rossoneri to the Europa League where they would be eliminated in the first knockout round.
But they faced FA Cup-winners Portsmouth in the group stage and only two goals in the final six minutes salvaged a 2-2 draw having been two-goals behind.
Champions League quarter-final, 2011: CHELSEA vs. Manchester United
Despite winning the Premier League and FA Cup in his first season, Ancelotti’s record with Chelsea in Europe left a lot to be desired.
Against United, his side lost 1-0 at home and 2-1 away – just as against Inter the previous campaign.
Champions League group stage, 2014: REAL MADRID vs. Liverpool
At this stage, Ancelotti had become the competition’s most successful manager while Liverpool had dipped so much they finished below Basel in this group.
Holders Madrid won 1-0 at the Bernabeu and 3-0 at Anfield.
Champions League last-16, 2017: BAYERN MUNICH vs. Arsenal
By quite some distance the easiest tie Ancelotti has had against and English team – and Arsenal’s last taste of the Champions League to date.
Bayern won 5-1 in both ties reach the quarter-finals with a 10-2 aggregate margin.
Champions League group stage, 2018: NAPOLI vs. Liverpool
In one of the most controversial ties, the second meeting ensured eventual winners Liverpool qualified at Napoli’s expense – though only after some questionable refereeing decisions.
Napoli had won 1-0 at home but Liverpool qualified in second place courtesy of their superior goal difference.
Europa League quarter-final, 2019: NAPOLI vs. Arsenal
There was a lot of anticipation for this tie but Napoli were second best throughout.
Arsenal won 2-0 at home and killed the tie off with a 1-0 win in Naples.
Champions League quarter-finals, 2022: REAL MADRID vs. Chelsea
One of Madrid’s best performances of the season followed by one of the worst saw Los Blancos sneak through.
A Karim Benzema hat trick put Madrid in control with a 3-1 win at Stamford Bridge but Chelsea were 3-0 up in the Spanish capital before a late goal forced extra-time and the hosts got another to win the tie.
Champions League semi-finals, 2022: REAL MADRID vs. Manchester City
Simply one of the all-time great Champions League ties. A chaotic first leg saw City edge to a 4-3 win at home and they looked to be reaching the final as they led 1-0 in Madrid going into stoppage time.
But two goals from Rodrygo sent the tie to extra time and Benzema gave Madrid the win from the penalty spot.
Wasn’t he manager of Napoli when they got 4 points from the 2 Liverpool group games in 2019 as well? I think he was.
The worst one was undoubtedly the 2005 CL final, collapsing to a bang average Liverpool team.
The loss to Man Utd in 1999 was no surprise either, given how awful Juve were that season.
Liverpool will be favourites in a few days, but RM have a decent chance.
@Ferban, yes, he was. Napoli only lost once to Liverpool in those 2 seasons.
I agree with you that Liverpool are seen as the favorites for obvious reasons: their high intensity style of play, a more vibrant youthful team and of course the English media hype that has been surrounding them for the last few years.
But Ancelotti and Real Madrid have so much experience and quality and they know a thing or two about playing a CL final.
@Milanista82
Yes, Napoli did pretty well under him v Liverpool, one of the few teams to stand up to them in this era.
RM aren’t the great force they were, but can still win tomorrow. I remember he changed Napoli to a 4-2-2 v Liverpool once to stop their full-backs from coming forward, and it worked very well. I can’t see who’d play in that formation for RM, though, if he wants to do it again.
Keeping Liverpool’s front 3 and 2 full-backs quite(ish) could be the key.
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