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: 10/10Squad Strength: 9.5/10Path 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.

#2 AC Milan 1989-90

Milan successfully defended their title after beating Benfica in the final

Goals Scored: 12 (in 9 games)Goals conceded: 3 (in 9 games)Legacy: 10/10;Squad Strength: 9.5/10;Path Difficulty: 9/10;

Milan are the last club to successfully defend the European Cup, and they did so in, ‘89-90. Having a squad that ranks right along the very best in football history, with a defense line which is, by consensus, the greatest ever, Milan laid their stamp on continental football in the late ‘80s and early ‘90s with an imprint that will impact football for generations to come.

Coached by the inimitable Arrigo Sacchi, who took a team of talented players and turned them into world-beaters within a span of 2 years, they brought a brand of entertaining football that completely changed the perception of Italian football elsewhere. They, however, failed to win the Serie A title that season, losing out to Maradona-led Napoli in the Serie A.

The Rosseneri breezed past HJK 5-0 in the first round, setting the tone for the rest of the campaign. Facing Real Madrid in the second round, they did a job on them at the San Siro, beating them 2-0, before keeping Quinta del Buitre at bay and limiting them to a single goal at Bernabeu.

Belgian outfit Mechelen proved to be unexpectedly tough opponents, holding Milan goalless for over 180 minutes. It took a moment of brilliance from van Basten in the second half of extra time for them to break the deadlock, and Simone sealed the tie with 3 minutes of extra time to spare.

The semifinal with Bayern Munich was another epic contest. Milan took a 1-0 lead from the San Siro to Munich, where again extra time was played. Borgonovo scored for Milan in the first half of extra time, giving them a 2-goal cushion for 20 minutes. Bayern did strike back to make it 2-2 on aggregate, but Milan shut them out after that to progress to the final on away goals.

The final, against Benfica, was a much closer affair than the game the Rossoneri played in Nou Camp the year previous. Frank Rijkaard got the decisive goal in the second half, capping off another great season on the continental stage for the red-and-black brigade, whom everyone in Europe now feared.

#3 Real Madrid 2013-14

Carlo Ancelotti guided Real Madrid to the elusive ‘La Decima’ in the 2013-14 season

Goals Scored: 41 (in 13 games)Goals conceded: 10 (in 13 games)Legacy: 9.5/10;Squad Strength: 9.5/10;Path Difficulty: 8.5/10;

Real Madrid gave football fans the greatest season on the offensive end in the Champions League, plundering 41 goals in 13 games at 3.15 goals/game. Cristiano Ronaldo helped himself to 17 in 11, smashing the previous individual record of 14. The legacy of this season is enhanced by the fact that this was the long-awaited La Decima which had been bugging everyone associated with the club ever since the 9th had been won in 2002.

Having been drawn alongside Galatasaray, Juventus and Copenhagen, Madrid breezed past the group stages of the tournament, racking up 16 points and 20 goals, with a minimum of 2 goals in every game. Facing Schalke in the round of 16, Madrid laid down a marker for the rest of Europe in the first leg, putting 6 past the Rhinesiders at their home turf, before winning the second leg 3-1 at home.

Dortmund provided them with a few jitters, however, in the quarterfinals. Madrid won their home leg 3-0, but with Cristiano Ronaldo absent in the second leg and di Maria missing a penalty, Dortmund went 2-0 up by halftime in the second leg. Los Merengues held on to their slender one-goal lead in the second half to progress to the semifinals.

Bayern Munich, defending champions from, ‘12-13, were favourites going into the tie, but Real Madrid gave them a lesson in football. Winning the first leg 1-0 at the Bernabeu, they proceeded to dismantle the Bavarian outfit 4-0 at the Allianz Arena, giving Pep Guardiola what he called his ‘worst day in office’. This game gave a resounding statement of superiority to the rest of Europe.

The final was another classic encounter. In the first ever derby final of the Champions League, Atletico Madrid took the lead in the first half via Diego Godin, and looked to be running away with the title before Sergio Ramos equalized with a bullet header from a corner in the third minute of second-half stoppage time. The Rojiblancos ran out of steam in extra time, and goals from Bale, Marcelo and Ronaldo gave Madrid a 4-1 scoreline at the end of extra time.

#4 AC Milan 2002-03

AC Milan beat Juventus in the penalty shootout to win the Champions League title

Goals scored: 21 (in 17 games);

Goals conceded: 14 (in 17 games);

Legacy: 8/10;

Squad Strength: 9.5/10;

Path Difficulty: 10/10;

The early 2000s were a tumultuous period in European club football. With no single team clearly better than the others, and a number of all-time greats playing for a number of teams across the continent. Milan’s own squad was one of the strongest around.

Having signed Rivaldo from Barcelona in the summer transfer window of 2002, post the World Cup, they bolstered their already strong strike force comprising of Shevchenko and Jon-Dahl Tomasson.

Milan got past the first group stage comfortably with 4 wins on the trot, in a group comprising of Depor, Bayern and Lens. The second group stage saw them face Real Madrid, Dortmund and Lokomotiv Moscow, whom they negotiated again with 4 wins in their first 4 games.

Having successfully navigated 2 tricky group stages, they faced Ajax in the round of 16. After a tight, tense first leg that finished goalless, Milan beat Ajax 3-2 in a classic encounter, having to wait till stoppage time for Tomasson to get them the winning goal (they were crashing out on away goals, with the scoreline at 2-2).

Having drawn Inter in the semifinals, the first leg was another tepid, tight affair which finished as a goalless draw (Inter was allocated home status for the first leg), Milan made it to the final with a 1-1 draw in their home leg. Shevchenko scored in first-half stoppage time, but Obafemi Martins’ late equalizer set the tone for an epic finale, in which the Rossoneri held on grimly.

The final also remained 0-0 over regulation and extra time, before Dida pulled off 3 saves off Trezeguet, Montero and Zalayeta to give Milan the edge in the penalty shootout. Shevchenko stepped up and converted the decisive 5th penalty for Milan, yielding one of the most iconic images in Champions League history.

#5 AC Milan 2006-07

Stung by the events of Istanbul from only 2 seasons before Milan won the title this time

Goals Scored: 20 (in 13 games)

Goals conceded: 10 (in 13 games)

Legacy: 7/10;

Squad Strength: 9/10;

Path Difficulty: 8.5/10;

The Calciopoli scandal which rocked Italian football in 2006, and continues to affect them to this day, caused a mass exodus of elite talent from Juventus, who were relegated, while Milan were docked 8 points in the league table for the season.

This made it nearly impossible for them to win the league, so Ancelotti got his side to focus on the Champions League, reaping rich rewards for it. Topping a relatively weak pool comprising of Lille, Anderlecht, and AEK Athens, Milan then made it past Celtic in the round of 16 1-0 on aggregate, negating the threat posed by Nakamura and co.

They then moved into top gear in the quarters against Bayern, drawing 2-2 at the Allianz Arena before beating them 2-0 at home with goals from Inzaghi and Seedorf. Beating Bayern was no mean feat, considering they had knocked out Real Madrid in just the previous round.

Faced by Sir Alex’s Manchester United in the semifinals, most fans expected them to lose out to the star power of Cristiano Ronaldo and Rooney. Milan, however, had other ideas, and despite losing 3-2 at Old Trafford in the first leg (Kaka scored a sumptuous brace), they closed United out in the second leg with a 3-0 victory.

Gattuso did a job on their forwards while Kaka’s and Seedorf’s first-half strikes all but guaranteed them a place in the final.

Stung by the events of Istanbul from only 2 seasons before, there was an air about the Milanello as they took the pitch in the rematch with Liverpool and ran out 2-1 winners in regulation time. Inzaghi displayed his typical poacher’s instinct to put Milan in the lead in the first half before a Pirlo free kick deflected into the net off him late in the second half.