Associazione Calcio Milan did not repeat its successful season in 1998–99, and fell back to third in Serie A, as well as crashing out of the Champions League, following a lackluster performance in the First Group Phase. In fact, Milan ended up last in the group, and was not even qualifying for the remainder of the UEFA Cup.

Andriy Shevchenko played his first season with the Milanese club, and managed to become top scorer already in his debut season. The Ukrainian further enhanced his reputation as a fearsome striker, which was fortunate for Milan, considering Oliver Bierhoff's scoring tally's decline. The team showed signs of being over the hill, having had several aging players while it won the league in 1998–99.

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

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