Madrid's Ancelotti a reminder of Milan's glorious past and uncertain present

Crowned kings of Europe seven times, only Madrid have won the Champions League more times than Milan, whose last triumph came under Ancelotti way back in 2007 when a star-studded line-up comfortably beat Liverpool. That team featured the likes of Paolo Maldini, Kaka and Filippo Inzaghi and was of a completely different league to the one that currently turns out at the San Siro.
And Ancelotti, 65, is also adored as the man who led Milan to the 2003 triumph, which came after a gruelling penalty shootout win against fierce rivals Juventus. "It will be a special match given my past," Ancelotti said to Sky in Italy on Monday. "I think it will be a good match. Milan haven't started well but they've got a good squad with a lot of talent."
Since Milan's triumph in Athens 17 years ago Madrid have won the Champions League six times, three of those victories coming with Ancelotti in the dugout. Meanwhile Milan's best run in the competition since was to the 2023 semi-finals, an impressive campaign which was soured by being comprehensively beaten in the last four by local rivals Inter Milan.
Ancelotti is a Milan icon not just for the two Champions League triumphs won during his eight years as coach but also for his exploits as a player in red and black. A classy midfielder, Ancelotti was the lynchpin of the Milan team which under Arrigo Sacchi revolutionised Italian football and won the old European Cup in 1989 and 1990.
Probably his most memorable moment in a Milan shirt came in the 1989 semi-finals when the Italians destroyed Madrid 5-0 in the second leg at the San Siro. Ancelotti put Milan ahead in the tie with a rocket of a shot and from there Frank Rijkaard, Marco Van Basten, Ruud Gullit and Roberto Donadoni contributed to a crushing victory still spoken about today as the club's best ever performance.

Back then Milan were football's bleeding edge and supplied with mountains of cash by Silvio Berlusconi, but today the sport's European capital is Madrid. Milan will step out at a completely refurbished Bernabeu while their own stadium projects remain little more than artists' renderings and face the sort of players who once upon a time would have turned out at the San Siro.
Madrid are not having their best campaign, as highlighted by the fearful hammering dished out to them by Barcelona less than a week ago, but they're operating on another level to Milan whose hopes of reaching the Champions League knockouts are still in the balance.
Just three points collected from three fixtures have left Milan in 25th place, one of 11 teams in the new league phase who currently wouldn't even reach the play-offs for the last 16. And Paulo Fonseca's side will walk out at the Bernabeu out of sorts and expected to leave Spain with the same number of points with which they arrived.
Milan have failed to come to life in the early part of Fonseca's reign and already trail Serie A leaders Napoli by eight points, albeit with a game in hand. It has been a campaign filled with rancour and rumours of dressing room bust-ups, in particular with his countryman and star winger Rafael Leao who is set to start in Madrid.
Leao has been benched for Milan's last three Serie A fixtures, a move which Fonseca has insisted on more than one occasion is not punishment for poor attitude and sub-par performances. "It's not a player's status that goes out on the pitch, I choose my team on the basis of what the team needs," said Fonseca after Milan's 1-0 win at Monza on Saturday.
If Milan are to get anything from the Bernabeu they will need a performance from misfiring Leao who is their only player capable of reaching the heights achieved by Vinicius and company.