AC Milan's hopes of advancing in the UEFA Champions League were dashed following a series of critical misjudgments during their playoff against Feyenoord. The turning point came just five minutes into the second half when defender Theo Hernández received a second yellow card for a reckless dive, leaving Milan with ten men. This premature exit from the tournament was not just about the sending-off; it highlighted a broader pattern of poor decision-making that plagued the team throughout the match.

Milan entered the second leg of the playoff needing a two-goal win to advance, having lost the first leg. They initially took control of the match, scoring early through new signing Santi Gimenez. However, the situation quickly spiraled out of control as Hernández's reckless actions shifted the momentum in favor of Feyenoord. Despite being one goal up and dominating the first half, Milan's inability to capitalize on their advantage became evident once they went down to ten men. The team, which had been poised to score again, suddenly found themselves on the back foot, struggling to maintain their composure.

Head coach Sérgio Conceição attempted to shift tactics after the red card, but his decisions only compounded the issues. Substituting key players like Christian Pulisic and Gimenez while keeping less effective players on the pitch raised eyebrows. As Feyenoord rallied, they equalized through Julián Carranza, ultimately sealing Milan's fate. The frustration boiled over, leading to further indiscipline from Milan players, which underscored the team's chaotic state during this crucial match. This defeat not only eliminated Milan from the Champions League but also raised serious questions about their decision-making on the pitch, leaving fans and officials alike to wonder what went wrong.