Arsenal vs AC Milan Tickets

For much of the history of the re-branded UEFA Champions League, which replaced the European Cup competition in 1992, both Arsenal and AC Milan have been a nearly ever-present presence in the competition, though clearly of the two teams, only one has achieved tangible success, while the other has spent a number of recent campaigns out of the mix.

Arsenal have appeared in the UEFA Champions League on 19 occasions up until 2023/24, with the vast majority of these coming in one unbroken spell between 2003/04 to 2016/17, a period where Arsene Wenger virtually guaranteed action in the showpiece tournament. In this era, the club never failed to get through their initial group stage but then stuttered in the knockout stages.

This led to four eliminations at the hands of both FC Barcelona and Bayern Munich. It also saw the Premier League side beaten in the 2006 final by FC Barcelona in Paris and visits to another Semi-Final and no less than four Quarter-Finals. All of which is a testament to the consistency achieved during Wenger’s lengthy time in charge.

However, the ultimate prize was never garnered, and Mikel Arteta will be looking to right that wrong and will hope to have learned from those; after all, in each of his five seasons as an Arsenal player, he was part of the set-up that were beaten in the competition.

AC Milan, on the other hand, can point to a great many successes in both the European Cup and its successor, the UEFA Champions League. The Rossoneri were beaten finalists in only their second European Cup campaign, when they were beaten by the all-conquering Real Madrid side of the era in 1957/58.

Five years later, they emerged victorious when they beat Benfica at Wembley in 1963, and in 1969, they won again, this time beating Ajax in Madrid. It would take another 20 years for the Serie A side to taste success, but when they did, it was well worth waiting for.

In 1988/89, the great Arrigo Sacchi’s side thumped Steaua Bucharest 4-0 in one of the most celebrated finals ever. Dutch masters Ruud Gullit and Marco van Basten both scored twice in the victory over their Romanian opponents. The following year, they won again, beating Benfica again in Vienna, and their first triumph of the UEFA Champions League format wasn’t far behind.

This time, another 4-0 win against FC Barcelona was achieved in 1994 with Fabio Capello at the helm. 2002/03 brought another success, a penalty shoot-out needed to beat Juventus this time before AC Milan suffered that horrendous loss to Liverpool in Istanbul in 2005 in a game they had led 3-0 in before capitulating.

Carlo Ancelotti gained revenge for that defeat two years later as they beat the Merseyside outfit 2-1 in Athens, and since 2007 and up until 2023, they have struggled to make a sustained impact on the tournament, only once getting as far as the Semi-Finals in that period.

Arsenal vs AC Milan Head-to-Head

Arsenal and AC Milan have met in three different European campaigns with mixed fortunes for both sides. In 2007/08, Arsenal eased to victory in their Round of 16 tie, with Cesc Fabregas and Emmanuel Adebayor scoring late on in the San Siro to secure a 2-0 aggregate win.

Then, in 2011/12, the tables were turned somewhat. This time, AC Milan thumped Arsenal 4-0 on their home turf to take a commanding lead to the Emirates Stadium, which, astonishingly, Arsene Wenger’s side almost turned around. Laurent Koscielny, Tomas Rosicky, and Robin van Persie all scored in the first half, but try as they might, Arsenal couldn’t find that crucial fourth goal and were, therefore, eliminated.

In 2017/18, the two sides played each other in the UEFA Europa League Round of 16, and Arsenal picked up a very useful away win, secured via a 2-0 win thanks to goals from Henrikh Mkhitaryan. In the second leg, Arsene Wenger’s side won 3-1 to complete a 5-1 aggregate rout.

Arsenal vs AC Milan Connections

There have not been an abundance of players to be fielded by both Arsenal and AC Milan, though one player who did so is French midfielder Mathieu Flamini. The former Marseille man appeared for Arsenal in 246 games across two spells, securing three FA Cup Winners’ medals and, in between, enjoyed five seasons in Milan, where he made 123 appearances and won the Serie A title in that period.