Milan's strong connection with European success was evident from day one. It played in the very first European Cup and was paired to play German side Saarbrücken. It lost the opening game at the San Siro 4-3 but won the return match 4-1. Three of those goals came in a powerful nine minute burst. Milan was the only one of the eight first round winners to overcome a first leg deficit and in that one conceded at home. This would very much be a sign of things to come. Milan smashed Rapid Vienna in the second round to book a semi final berth with Real Madrid. Milan lost the opening match 4-2 at the Bernabeu in front of 129,690 fans. It won the return match 2-1 but it wasn't enough.
Milan was back two years later and made it all the way to the final. On its way to the final it defeated Rapid Viena, Rangers, Borussia Dortmund and Manchester United. Standing between it and the trophy was Real Madrid. The final was full of stars – Milan has Cesare Maldini, Nils Liedholm and Ernesto Grilo while Madrid had Alfredo Di Stefano and Raymond Kopa. After a scoreless first half, Milan went ahead. The side then traded three goals in five minutes to send it to extra time. There Francisco Gento scored the winner to hand Real its third straight title.
Two years later Milan made an early exit at the hand of Barcelona. The in 1962-63 it fought back to meet Benfica in the final. Again Milan was playing a side looking for its third straight title. The final was at Wembley and many thought Benfica would make it three on the trot after Eusebio scored in the 18th minute but Jose Atlafini scored a second half double to see Milan become the first Italian side to win the world's most prestigious club competition.
Its defence of the title was cut short by Real Madrid in the quarter-finals. It would be five years until Milan returned to the tournament and it made it a memorable one. It took out the two previous winners, Celtic and Manchester United to book a date with Ajax in the final. The time of Ajax and a 21 year old Johan Cruyff would come. This night in Madrid was to be Milan's and a Pierino Prati hat-trick made sure of it.
Milan's defence was ended when Feyenoord exacted revenge for its fellow Dutch club. It took out Milan on its way to a strong time in Dutch football.
It would be 10 years until Milan returned to the European Cup. The rustiness showed when it was eliminated 1-0 by Porto. Another long break followed but when the drought was broken Milan was ready to reclaim its title as one of Europe's most dominant side. It made its way to the final and did so with a semi-final win over long time rival Real Madrid. Milan was played a Steaua Bucharest side that had won three years earlier and had the likes of Marius Lacatus and Gheorghe Hagi. Milan had a trio of talented Dutchmen in Frank Rijkaard, Marco Van Basten and Ruud Gullit. It also had a young Paolo Maldni and Alessandro CostaCurta. It was 3-0 to Milan at the half and Van Basten added a second along to the two that Gullit had earlier scored. The victory signaled that Milan was back.
It sent even more of a signal the following year when it successfully defended the title. What would a campaign in Europe be without a stop in Madrid. Milan defeated them in the second round and needed extra time to get by Bayern Munich in the semi-finals. The final was in Vienna and again it was a Dutchman who scored. This time Rijkaard scored the winner. This is the last time someone has successfully defended the trophy.
Milan's hoped of making it three in a row were dashed by Marseille in the quarter finals. As they would be again in the first Champions League final. Forced to wear its more orthodox red and black stripes, Milan never clicked and lost 1-0 to the French.
The following year, Milan made it back to the final which was in Athens against Barcelona. Marcel Desailly had played in Marseille's final winning team the year before and was now with Milan. Another change was that Milan was back to wearing its all white strip for the final. Whether this made a difference or not, who really knows, but Milan smashed the Spanish 4-0.
Its hopes of successfully defending its title went all the way to the final but there, they were extinguished by Ajax which defeated it 1-0.
Then the proud club hit somewhat of a rough period. In 1996-97, it couldn't get out of a group which contained Porto, Rosenborg and Gothenburg. The Norwegians defeated Milan in Milan to knock it out. The same thing happened three years later when it was last to Chelsea, Hertha Berlin and Galatasaray.
In 2002-03 it bounced back. It defeated old foes Ajax in the quarter-finals before defeated even older foes Inter Milan in the semi-finals. The set up an all-Italian final against Juventus. Played at Old Trafford, the game was a pretty dull affair and without any score went to penalties. Both sides missed two of their first three shots but then Milan didn't miss again. Andriy Shevchenko kicked the winning one to send Milan its fifth victory.
Two years later, Milan was back in the final. This one was in Istanbul against Liverpool. This was one of Europe's greatest ever nights and for once, Milan was on the wrong side of the ledger. Maldini opened the scoring after just one minute and Hernan Crespo scored twice before half time to give Milan what looked like an unassailable 3-0 lead. Liverpool replied with three goals in a six minute burst to send the game to extra time and then to penalties. Milan missed its opening two shots and when Shevchenko missed it was all over. He had experienced the joy of kicking the winning penalty and the agony of kicking the losing one.
Milan would bounce back as it did two years later. It reached the final where it would find itself in a rematch with Liverpool. Milan had already won one final in Athens and was looking to make it two. Filippo Inzaghi scored a double and redemption had come to Milan for that night in Istanbul.