1999–2000 A.C. Milan season

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.

1999–2000 A.C. Milan season

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.