AC Milan has one of the most storied histories in Italian football with a long list of accomplishments that includes Serie A titles, Champions League trophies, and much more. However, there have been some low points for the club, with these five moments perhaps being the worst for AC Milan fans.
Europa League Bouncing
The Champions League is where the best UEFA teams compete, while the Europa League is the secondary tournament. Those who have expectations of the Champions League like Milan could see it as a bit of a consolation, but the players still take the tournament very seriously. In the 2018-19 edition of the tournament, Milan still had high hopes during their financial rebound (more on that later).
During the group stage in the round of 32, however, Milan didn’t play their best. In their six matches, AC Milan won just three games while drawing one and losing two. Milan finished tied for second with Olympiacos but had a goal differential of just +3. It knocked them out of the tournament and set a low point for the modern era of AC Milan football.
The 1990-91 Euro Ban
The 1990-91 European Cup was an interesting one for AC Milan. The club was the only team to qualify for the second round after Ajax’s spot was vacated. Milan was the two-time defending champion, and they were expected to compete once again. Milan ran into Club Brugge in the round of 16 but only won 1-0 on aggregate over two legs. In the quarterfinal, Milan squared off against Marseille.
The two clubs drew in the first leg 1-1 with Ruud Gullit scoring for Milan and Jean-Pierre Papin scoring for Marseille, with both goals coming in the first half. During the second leg, Marseille was up 1-0 when half of the floodlights in Stade Velodrome went out. When the power came back on after 15 minutes, Milan refused to come back on the pitch. This earned Marseille a 3-0 awarded victory with Milan receiving a one-year ban from European competition.
Financial Troubles Lead to Near-Ban
While the European Cup resulted in a finalized ban, there was a proposed ban many years later that the club nearly suffered. Between the end of 2015 and the summer of 2017, AC Milan reported a net loss of €146 million. This was well in excess of the €25 million allowed by UEFA’s Financial Fair Play Regulations. The result was a €12 million penalty and a proposed one-year ban from European competition.
The club was able to get the ban lifted, thankfully, but it opened a lot of eyes to just how much Milan was spending in hopes of bolstering the roster. Milan had until June 2021 to break even, which they did. The process took away some of the star power that Milan was able to afford previously, but they rebounded quickly after the penalties came down and ended up winning the 2021-22 Serie A title.
2005 Champions League Final
Some of the most heartbreaking moments in sports come when a team or individual has a massive lead, only to see it dwindle away and result in a loss. It hurts even more when there’s a massive prize on the line. That was the case for AC Milan at the 2005 UEFA Champions League final. The club had gotten through the group stage rather easily and then defeated Manchester United and rival Inter Milan handily.
After sneaking by PSV Eindhoven in the semis, they took on Liverpool for the title. Milan struck in the first minute with a Paolo Maldini goal, then Hernan Crespo added two more in the final six minutes of the first half. It looked like the match was all but over, but Liverpool stormed back hard. Steven Gerrard, Vladimir Smicer, and Xabi Alonso all scored in a seven-minute span to force extra time. Neither team scored, sending it to penalties where Liverpool won 3-2.
There have been a handful of big match-fixing scandals throughout Serie A history, and one of the big ones came in the form of Totonero 1980. The scandal included Milan and a handful of other teams from both the top league and Serie B. Milan and Lazio took the biggest punishments with both clubs relegated to Serie B while other clubs were penalized points and some individuals were banned or even imprisoned.
Milan didn’t waste much time getting back into Serie A, however. In their one season with Serie B, the club finished with 50 points in 38 games. Along with Genoa and Cesena, they made the move back up. The long road back to the top of Serie A concluded with a league title in the 1987-88 season that saw them finish three points ahead of Napoli.