In 2005–06 season Associazione Calcio Milan had a rather modest season compared to its previous seasons, before being rocked by a minor involvement in the 2006 Italian football scandal, where rivals Juventus was relegated and stripped of two league titles. Due to Milan's involvement it did not inherit either of the titles, instead being penalised and dropped down the 2006 order, initially out of European football, but later reinstated into fourth, which meant Champions League qualification, a tournament Milan then went on to win. It did have to start the 2006–07 league season with an eight-point deduction, which further complicated hopes of a new league title.

On the pitch in 2005–06, Milan was not able to challenge Juventus for the virtual league title, then going out against Barcelona in the Champions League.

Following the season, the club sold Andriy Shevchenko for €40 million, the highest fee paid for a player turning 30 in the same year, to English club Chelsea.

Note: Flags indicate national team as defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.

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