AC Milan needing to win their final game in order to secure a Champions League spot is nothing new.
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Milan go into their last match of 2025-26 with a rather simple equation: they must emerge victorious against Cagliari to ensure that they finish third. With that comes a return to the top European club competition, which is a huge boost for the plans of Massimiliano Allegri and the management.
Win-and-in situations are not something that Milan are strangers to, even if a draw could be enough on Sunday. In fact, it has happened twice in recent memory.
May day in Siena
Back on 19 May 2013, Milan entered the final day in third place (the final Champions League play-off spot at the time). They trailed second-placed Napoli but held a narrow two-point lead over fourth-placed Fiorentina. La Viola won their final match convincingly to put the pressure on.
Meanwhile, the Rossoneri fell 1-0 behind to an already relegated Siena side. Things went from bad to worse when captain Massimo Ambrosini was sent off in the 69th minute for a second yellow card, with the players looking totally defeated.
With just seven minutes left, Milan were staring down the barrel of a fourth-placed finish and Europa League football for the 2013-14 campaign, which could have had a big impact on Massimiliano Allegri’s immediate future and that of other stars.
Then, the fightback came just after the home side went down to ten men themselves. Mario Balotelli equalised from the penalty spot in the 84th minute after a clumsy hold inside the box, despatching it with his trademark composure from 12 yards.
Just three minutes later, centre-back Philippe Mexès had an initial shot saved and then bundled in the rebound to complete the comeback and seal a 2-1 victory, securing Milan’s Champions League status in dramatic fashion.
Night and Dea
The other time Milan took it down to the wire was on 23 May 2021. After leading the Serie A table until mid-February, a late-season collapse left Milan hanging onto their top four spot, with Atalanta, Napoli and Juventus breathing down their neck.
The Diavolo beat Juventus and Torino within four days and 10-0 on aggregate (3-0 vs. the Bianconeri, 7-0 vs. the Granata). It left them with a simple equation: beat Cagliari at home (sound familiar?) in round 37 to secure UCL.
So, Milan traveled to Bergamo to face Atalanta knowing only a victory would guarantee a return to Europe’s elite after a painful seven-year absence. They had to do it without the injured Zlatan Ibrahimović, too.
Perhaps unexpectedly given the form and opposition, Milan handled business well. Franck Kessié converted two penalties – one right before half-time and another right at the end – to obtain a 2-0 victory that saw them leapfrog Atalanta to finish as the Serie A runners-up.
Will the Cagliari game yield another night of drama like in Siena, or will it be a professional performance like against Atalanta? Or, could the collapse even be completed with a draw or defeat?