The match was largely uneventful until the finals minutes when Ajax took a well-deserved lead after a header from defender Stefano Denswil in the 90th minute. In stoppage time, Milan drew level via a Mario Balotelli penalty.
Ajax started the match quite composed despite the average age of the starting XI being only 23 years old, even if they did not put a shot on goal until the 5th minute when Sigthorsson’s near post shot was saved by Christian Abbiati. They were largely able to keep the ball as Milan seemed content to give them possession.
The first 15 minutes saw Ajax enjoy the majority of possession without causing the Rossoneri too many problems as Max Allegri’s men sat back and let Ajax pass the ball in front of them. Milan offered virtually nothing going forward early on, with strikers Balotelli and Robinho barely getting a touch on the ball.
Ajax goalkeeper Jasper Cillensen didn’t get his gloves dirty until a half hour in when he snatched up Kevin Constant’s low cross after getting in behind Ricardo van Rhijn. The Amsterdamers nearly took the lead twice in one minute when Abbiati parried Lerin Duarte’s freekick over the bar and then Niklas Moisander’s volley off the ensuing corner went high.
Milan’s one sustained attack in the first half ended with Balotelli on the ground in the area, however, the referee waived play on after some pretty blatant embellishing on the Italian international’s part. The visitors were unable to record a solitary shot on the Ajax goal in the first 45 minutes.
The Rossoneri started the second half much more proactively, registering their first shot of the match two minutes after the break with Montolivo seeing his shot stopped by Cillensen after Constant’s cross into the area. Milan slowly pulled themselves back into the match, attacking Ajax with much more purpose.
Ajax could have drawn first blood in the 55th minute when an excellent van Rhijn cross met the head of Sigthorsson, however, his shot fell right into Abbiati’s arms.
Milan almost took a surprise lead a couple minutes after the hour mark when Balotelli’s curling shot beat Cillensen but could not beat the far post as it clanked off the upright. Milan played better after Balotelli’s effort, putting the young Ajax squad on the backfoot but could not convert possession into goals.
The final 15 minutes saw Ajax defending deeper and deeper as Milan piled on the pressure. The Rossoneri had another penalty shout waived away after Balotelli was tugged down in the area by defender Mike van der Hoorn. Former Ajax player Urby Emanuelson almost scored against his ex club but Cillensen was up to the task, acrobatically saving his near post shot.
Ajax almost pulled off the upset after Sigthorsson’s shot went in, however, Lasse Schone was adjudged to have handled inside the area during the build up.
The Amsterdamers finally broke through in the 90th minute when Stefano Denswil scored off a corner kick, powering header past a frozen Abbiati.
In an exciting end to the match, van Rhijn cleared the ball of the line after a Milan shot almost snuck over the line. Then, Milan won a penalty in stoppage time after van der Hoorn was adjudged to have dragged Balotelli down in the box, with the striker duly converting his spot kick.