Following Capello's departure after the 1995–96 title win, as well as the aging and retirement of certain key players, Milan faced dark times in their history. Milan were defeated in the 1996 Italian Supercup Final by 1995–96 Coppa Italia winners Fiorentina, and the 1996–97 and 1997–98 seasons were negative, as Milan failed to qualify for Europe on both occasions. These fruitless seasons saw Milan undergo several managerial changes, including Tabárez, and the unsuccessful returns of Sacchi and Capello. However, Costacurta, through his leadership in defence, would help Milan reach the 1998 Coppa Italia Final, losing out to Lazio. With the arrival of Alberto Zaccheroni during the 1998–99 season, Costacurta continued to be a key member of the starting line-up, and featured in Zaccheroni's new three-man defence alongside Maldini and Luigi Sala. Costacurta was also named Milan's vice-captain that season, behind Maldini, following the retirement of Baresi and Tassotti. At the end of the season, Milan managed to capture their 16th "Scudetto" win, and Costacurta's sixth in total, finishing ahead of Lazio by a single point. However, the next two seasons would see Milan undergo yet another trophy drought. Milan would lose the 1999 Supercoppa Italiana to Parma, and would finish in third place in 1999–2000, and in a disappointing sixth place, outside of the Champions League spots, in 2000–01. Milan also suffered early eliminations in the first and second round of Champions League during those two seasons, and Zaccheroni would be sacked midway through the 2000–01 season, and replaced with Cesare Maldini as a temporary caretaker.