These teams have faced off 4 times before, or twice with the home and away formula. The first match was in 1995. At the time the European Supercup was played over two legs in the winter, not the single match that it is today. For the first match, the Rossoneri under coach Fabio Capello came back to Milan with a 0-0 draw played in London. In front of their own fans, the team recorded a 2-0 win wearing a yellow top for the occasion. Boban opened the scoring in the first half and Massaro made it two with a header in the second half, recording a memorable double after winning the Champions League against Barcelona in 1994.
Not such a positive result in 2008, the last time the two teams met. It was at the same stage in the Champions league and it was a Milan led by coach Carlo Ancelotti, who had won the trophy the season before. A certain Alexandre Pato was making his debut in the tournament on that night. It ended 0-0 in London but the return match at the San Siro on 4 March 2008, Wenger’s men put in a good performance to win 2-0 with 2 late goals from Fabregas and Adebayor.
Now the teams face off once again in the Champions league. Arsenal have a record of 5 wins, 2 draws and a single loss. After getting past Udinese in the preliminary stages of the competition, Arsenal topped Group 7 with 11 points, scoring 7 goals and conceding 6.
