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Ranking Carlo Ancelotti's Champions League-winning teams

Carlo Ancelotti has done some impeccable work in the biggest club championship of the planetTwo-time European Cup winner as a Milan player, 2 wins as their trainer and 1 as the manager of 2013-14 European champions Real Madrid, Ancelotti’s name is etched in the annals of Champions League history for all times to come.Whether it be as a defensive medio under Arrigo Sacchi or as the point man in the dugout, the Italian has done some impeccable work in the biggest club championship of the planet.Here, we rank all 5 of the Champions League-winning sides that he has been part of. The aim of the article is just to deduce the rank order of the best Champions League campaigns that Ancelotti has played a role in, irrespective of the amount of importance his role had.Parameters used to rank:(1) Path difficulty (out of 10) – a score of 10/10 implies that the team consistently beat world-class teams at all stages of the competition;(2) Squad Strength (out of 10) – a score of 10/10 indicates that the team is among the all-time great sides in football history;(3) Legacy (out of 10) – the higher the score, the greater the impact of the team’s players and tactics on teams in the future;Qualifying rounds, wherever applicable, have been disregarded. Only the performances from the group stages onward have been considered.The curious thing about all 5 of these campaigns is that although his teams emerged victorious in Europe, he didn’t win a league title in any of those seasons, which puts a dampener on all 5 of these victories. That, though, should take very little away from the performances of teams which are considered legendary by most standards.

#1 AC Milan 1988-89

AC Milan's Carlo Ancelotti holds the trophy after beating Steaua Bucharest 4-0.

Goals Scored: 20 (in 9 games)
Goals conceded: 5 (in 9 games)
Legacy: 10/10
Squad Strength: 9.5/10
Path Difficulty: 9/10

It is almost impossible to distinguish Sacchi’s first European success from his second, but the main reason we place the first one above the second is the manner in which Milan dismantled Steaua Bucharest in the final, with an emphatic 4-0 victory. Also, they were a more fluid attacking side in this first season when their style of play took the continent by storm.

Sacchi’s Milan introduced hitherto untested tactics like high pressure up the pitch and a high-line defense. They played a narrow 4-4-2, with each player in midfield tucking in and hassling opposition players on the ball and forcing the play wide, from where Maldini and Tassotti would keep the wingers in check. The onus was always on regaining the ball quickly.

Milan faced Bulgarian outfit Vitosha in their first round and comfortably beat them 7-2 on aggregate, with Marco van Basten scoring 4 past them in the second leg at home in a 5-2 win. The second round saw them locked in a tough fixture against Red Star. 

After a first leg that ended 1-1 at the San Siro, the tie went to penalties following a 1-1 scoreline after regulation and extra time. Milan had the ball crossing the line early on in the game, but the linesmen couldn’t spot it and thus the goal never counted. Goalkeeper Galli saved Milan the blushes by saving their last 2 strikes from Savicevic and Mrkela.

The third round was a tepid affair as the first leg between Germans Werder Bremen and Milan finished goalless, while the second leg was decided by a penalty converted by Van Basten in the first half to give Milan a 1-0 aggregate win.

The semi-final pitted Milan against the Real Madrid, led by Emilio Butragueno and Hugo Sanchez, who were considered to be the best strikers in Europe at the time. Sacchi, however, had other ideas, and Milan left Real reeling in the first leg, luckily hanging on to a 1-1 draw. Madrid bore the full brunt of Milan’s mastery in the second leg as they got walloped 5-0 at the Giuseppe Meazza. Ancelotti began the rout with a sumptuous opener from outside the box, and the game had 5 different scorers including Donadoni and Milan’s Dutch trio.

The final, of course, is one of the fairytales of European football. Maldini recalled in an interview that over 90,000 Milan fans were present at the Nou Camp, and this gave them the unshakeable belief that helped produce one of the great footballing displays in Europe.

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