FLASHBACK: AC Milan 5 â€“ Real Madrid 0, European Cup semi-final second leg, April 19, 1989
After drawing the first leg 1-1, the Rossoneri produced one of the all-time great performances to see off Madrid on their way to the first of two consecutive successes in the competition that marked them as the best team in Europe at the time.
Current Chelsea boss Carlo Ancelotti claimed the opener with a long-range snorter, Dutchmen Frank Rijkaard, Ruud Gullit and Marco van Basten scored the next goals before Roberto Donandoni completed the rout within an hour.
The Real Madrid side included the likes of Bernd Schuster, Hugo Sanchez and Emilio Beutrageno and were certainly no pushovers. Arrigo Sacchiâ€™s side would go on to win the final 4-0 against Steaua Bucharest with another display of fine attacking football.
Highlights of AC Milan’s famous defeat of Real Madrid can be seen here.
Real Madrid v AC Milan, Champions League, October 21, 2009
It may be a little early to say roles are reversed for the match-up at the Bernabeu, but it is fair to say it would be a major, major surprise if Leonardoâ€™s team were to emerge victorious on Wednesday night, let alone if they hit five past (100/1) Iker Casillas.
These two teams may be synonymous with the trophy, having won the competition 16 times between them but most of the stardust comes from the home team. Adding a little spice to the encounter is the return of Kaka, but in a sign of AC Milanâ€™s current state, some have billed this match: The Galacticos v “The Geriacticos.”
Kaka (7/1 to score a brace) will take top billing going into this match as he faces the club he spent six seasons and established himself in world football. The Brazilian played just 18 minutes of the win against Valladolid on Saturday night and should be raring to go against his old team mates. With Cristiano Ronaldo out with an ankle injury, Kaka has a lot more of the attacking responsibility and has already announced he will not celebrate should he score against AC Milan.
Real Madrid are sitting pretty in Group C having won both their matches so far and a win in this one will all but ensure their progression to the knock out stages. They rebounded from defeat to Sevilla before the international break by dismantling Valladolid with Raul scoring two early goals on his 711th appearance for the club.
Los Blancos will be hoping to repeat their 3-1 group stages victory of March 2003, that day Raul (5/1 to score first & Real Madrid win) also scored twice and Guti (10/3 to score) bagged the other and a similar scoreline looks very possible. From what has been seen of the Galacticos 2.0 project so far, it is fair to say this Real Madrid side are a lot more organised and have strength in depth in defence and in defensive positions in the midfield, which makes Milanâ€™s job very difficult.
The pressure on Leonardo eased with the 2-1 win over Roma on Sunday but progress in this competition is vital for the Brazilian, the club and beleaguered owner Silvio Berlusconi. Milan will be without Gennaro Gattuso due to injury and the snarling Italian will be missed to stem the white tide.
Dutch striker Klaas-Jan Huntelaar (10/3 to score) will be eager to impress after spending half a season at the Bernabeu. His total of eight goals in 20 games during half a season in Spain suggests he has the necessary quality although he is yet to score for Milan and will likely start on the bench.
For Milan, all eyes will be on Ronaldinho (12/1 to score first) as the buck-toothed wonder returns to the scene of one of his greatest performances. Barcelonaâ€™s 3-0 win at the Bernabeu in 2005 was greeted with applause by the home fans and still lives long in the memory.
With all the European trophies both sides have won, this match simply underlines how Real Madrid have much to look forward to whilst Milan can simply look back on past performances be it for the club or personally. The result should follow accordingly.
101gg predicts: Real Madrid 3 â€“ AC Milan 1 (10/1)
Full match odds here.