AC Milan, based out of the iconic San Siro in Italy, have been one of the most successful teams in recorded history. The Red and Blacks have achieved greatness status in Europe and Italy simultaneously and been one of the sides to look out for.
However, with changes in ownership and key figures leaving the club, they haven’t been quite able to live up to their high standards. We take a look at 10 games that AC Milan fans would like to forget.
10. Juventus 1 – 0 AC Milan, 2016 Copa Italia Final
Six Scudettos on the roll for Juve meant AC Milan were fading into irrelevance. The Rossoneri had a chance to prove a point in the Final of the Cup against Juve themselves.
But, a late goal from Real Madrid loanee Alvaro Morata meant Milan ended another season trophy-less.
9. Juventus 4 – 0 AC Milan, 2018 Copa Italia Final
Arch rivals Juventus were bonafide champions of Italy under the guidance of Massimiliano Allegri. Their fourth domestic double were firmly in their sights.
Milan could have hurt them real bad if they put together a better performance than the one they put in during their 4-0 defeat to Juve.
8. AC Milan 3 – 3(5 – 3) Liverpool, 2005 UEFA Champions League Final
Three goals in the first half for Carlo Ancelotti’s AC Milan meant they were clearly favorites to lift the Champions League in Istanbul.
However, Liverpool staged a brilliant comeback to draw level 3-3 and take the game to penalties which the British side won 5-3.
7. AC Milan 1 -6 Juventus, 1996-97 Serie A
Juve humbled AC Milan at the San Siro with 6 goals to one on a crazy night of football.
Vieri and Jugovic scored braces as Arrigo Sacchi’s team collapsed to their most humiliating defeats in the Serie A to Juventus.
6. AC Milan 0 – 3 Juventus, 2000-01 Serie A
Another classic Milan- Juve encounter with a result not in favor of Milan.
The reigning champions of Italy were having a torrid time in Europe and loss to Juve on a 3-0 margin meant Capello was in danger of being sacked. The Italian eventually got sacked and this defeat played a huge part in that.
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5. AC Milan vs Tottenham Hotspurs, 2010-11 UEFA Champions League Round of 16
Tottenham made the Champions League places for the first time in the 2009-10 season. They went on to feature in the Round of 16 against Milan at the San Siro.
Then Tottenham striker Peter Crouch’s goal meant Milan followed Inter in being eliminated from the competition at the hands of first-timers Spurs.
4. AC Milan 0 – 1 Vicenza, 2000-01 Serie A
After Fabio Capello’s stint at the helm of AC Milan was cut short by a string of poor results including a loss to Juve and then to Leeds United before failing to progress through the group stages of the Champions League.
He was replaced by Cesare Maldini, skipper Paolo’s father who brought about initial results.
However, Vicenza shocked him in a Serie A outing at San Siro with a 1-0 victory that proved extremely difficult to digest at the time.
3. AC Milan 0 – 4 Deportivo la Coruna, 2003-04 UEFA Champions League
Imagine winning 4-1 away in the first leg of the Champions League and yet failing to progress to the next round.
AC Milan suffered this fate as Spanish side Deportivo la Coruna came from behind on match control to win 4-0 on a night that defied logic at San Siro.
2. AC Milan 0 – 1 FC Barcelona, 2005-06 UEFA Champions League Semi-Final 2nd Leg
A controversial match to say the least, Milan had Andriy Shevchenko’s goal disallowed as Barca managed a 1-0 win at San Siro to knock Milan out of the competition.
The incident was preceded by Milan’s Calciopoli scandal that shook Italian football.
1. AC Milan 2 – 2 Werder Bremen, 2008-09 Europa League
One of the most disappointing draws/losses for Milan, this was the game that knocked Milan out of the European framework for the following year which led to the departure of star man Kaka to Real Madrid and the downfall of the Italian giants.
Bremen conceded two goals early but came back strongly to make it 2-2 at the San Siro and go through on away goals.