Real Madrid vs AC Milan: 5 Classic Champions League Matches

Real Madrid and AC Milan have faced each other several times in the UEFA Champions League over the years.
IMAGO / PanoramiC

Since the UEFA Champions League was created as the European Cup in 1955, Real Madrid and AC Milan have met 15 times.

Despite the limited number of matches, the two teams have produced some enthralling encounters over the years. From dramatic late goals to a memorable European Cup final in the 1950's, these two giants have plenty of history.

Both sides are set to add a new chapter on Tuesday night when reigning Champions League holders Real Madrid host Milan. But before we get there, let's revisit five classic matches between Los Blancos and Rossoneri, starting with their most recent encounter back in 2010.

5. 2010: AC Milan 2-2 Real Madrid

Pedro Leon
IMAGO / Insidefoto

In November 2010, Pedro Leon's 94th-minute second-half stoppage goal rescued a point for Real Madrid away at AC Milan.

Gonzalo Higuain had given Los Blancos the lead before a Filippo Inzaghi double stunned Jose Mourinho's men. However, Real dug deep and got their reward right at the death. That last-gasp goal secured Real place in the knockout stages of the Champions League with two group games to spare.

Despite advancing in the competition, Real Madrid was knocked out by rivals Barcelona in the semi-finals.

4. 2003: Real Madrid 3-1 AC Milan

Raul playing against AC Milan
IMAGO / Buzzi

The March 2003 Champions League encounter between Real Madrid and AC Milan saw Los Blancos triumph 3-1.

Two goals from Real legend Raul put the home side firmly in control. Rivaldo pulled a goal back for the visitors in the 81st minute before Guti sealed the win, boosting Los Blancos' chances of advancing to the knockout stages.

At the time, Real Madrid and Milan were competing in the second group stage of the Champions League. Both teams advanced, but Real Madrid was knocked out in the semi-finals by Juventus. Meanwhile, Milan went on to lift the trophy.

3. 2009: Real Madrid 2-3 AC Milan

Pato, Pirlo, and Kaka
IMAGO / Gribaudi/ImagePhoto

An 88th-minute winner from Pato saw AC Milan overcome Real Madrid 3-2 at the San Siro in 2009.

Los Blancos went into half-time with a 1-0 lead, courtesy of Raul. The second half then burst into life, with Pirlo and Pato scoring within four minutes of each other. Royston Drenthe responded for the home side 10 minutes later, but Pato's late volley ended Real's comeback hopes in the Group C fixture.

More disappointment followed as Manuel Pellegrini's men were eliminated from the competition by Lyon in the round of 16.

2. 1989: AC Milan 5-0 Real Madrid

AC Milan's Carlo Ancelotti heading the ball against Real Madrid
IMAGO / Buzzi

Not only has Carlo Ancelotti managed both Real Madrid and AC Milan, but the Italian has also scored in the fixture as a player.

In the second leg of the European Cup semi-final in 1989, Ancelotti opened the scoring as Milan cruised to a 5-0 victory. Frank Rijkaard, Ruud Gullit, Marco van Basten, and Roberto Donadoni also scored. Milan ended up winning the tie 6-1 on aggregate.

After brushing aside Real Madrid, Rossoneri went on to lift the trophy, defeating 4-0 Steaua Bucharest in the final.

1. 1958: Real Madrid 3-2 AC Milan (after extra time)

Real Madrid against AC Milan in the 1958 European Cup final
IMAGO / Belga

It doesn't get any bigger than this. The 1958 European Cup final, held in front of 67,000 fans in Brussels. With both teams playing out a 2-2 draw in normal time, the thrilling contest went to extra time.

In the 107th minute of extra time, Spanish football legend Paco Gento found the net and secured Real Madrid's third consecutive European Cup.

The result capped off a memorable campaign for Luis Carniglia's men, who also clinched the La Liga title for the sixth time.

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