Tabarez to Terim

1996-1997

After the departure of Fabio Capello in 1996, Milan recruited Oscar Washington Tabarez but they struggled under the new manager and were winless in their first few opening matches. In an attempt to regain former glories they brought back Arrigo Sacchi to replace Tabarez. Milan signed new players like Ibrahim Ba, Christophe Dugarry and Edgar Davids. Milan struggled and shockingly ended the Season 1996-97 in eleventh place in Serie-A.

1997-1998

Sacchi was replaced with Capello in the following season. Capello's new Milan signed many potential players like Christian Ziege, Patrick Kluivert, Jesper Blomqvist, and Leonardo but the results were even worse than the season before. The team suffered their worst Serie-A defeat, humiliated by Juventus FC at their own home of San Siro with a 1-6 score, although they ended Season 1997-98 an improved tenth place. This was still unacceptable and Capello, like Sacchi, was fired.

1998-1999

In their search for a new manager, Alberto Zaccheroni attracted Milan's attention. Zaccheroni was the manager of Udinese who had ended the Season 1997-98 on a high note in 3rd place. Milan signed Zaccheroni along with two of his players at Udinese, Oliver Bierhoff and Thomas Helveg. Milan also signed Roberto Ayala, Luigi Sala and Andres Guglielminpietro and with a 3-4-3 formation, Zaccheroni brought the club's 16th Scudetto back to Milan. The winning line-up was: Christian Abbiati; Luigi Sala, Alessandro Costacurta, Paolo Maldini; Thomas Helveg, Demetrio Albertini, Massimo Ambrosini, Andres Guglielminpietro; Zvonimir Boban, George Weah, Oliver Bierhoff.

1999-2000

Despite success in the previous season, Zaccheroni failed to transform Milan to the great team it used to be. The following season, despite the emergence of Ukraine's great Andriy Shevchenko, Milan disappointed their fans in both the Champions League and Serie-A. Milan exited the Champions League early, only winning one out of six matches (three draws and two losses) and ended the Season 1999/00 in the 3rd place. Milan was never a challenge to the top two contenders to the Scudetto, S.S. Lazio and Juventus FC.

2000-2001

The following season, Milan qualified for the UEFA Champions League 2000-01 by defeating Dinamo Zagreb to a 6-1 aggreggate. Milan started the Champions League at a high note, defeating Beşiktaş J.K. from Turkey and Spanish giants FC Barcelona, who at the time consisted of international world-class superstars in Rivaldo and Patrick Kluivert. But Milan's form began to seriously decline, drawing against a number of teams (which are seen as technically inferior to Milan), but mainly losing by a 3-0 scoreline to Juventus in the Serie-A and 1-0 to Leeds United. In the Champions League second round, Milan only won once and drew four times. They failed to beat Deportivo de La Coruña from Spain in the last game and Zaccheroni was fired. Cesare Maldini, the father of team captain Paolo, was appointed and things immediately got better. Maldini's official coaching debut at Milan started with a 4-0 win over A.S. Bari, who still had the young gun, Antonio Cassano. It was also under Maldini's leadership that Milan defeated their city rivals Internazionale with an outstanding score of 6-0, a score which has never been repeated and in which Serginho starred in the match. However, after this peak of form, Milan started losing again including a disappointing 1-0 defeat to Vicenza Calcio, with the only goal in the match scored by a young Luca Toni. In spite of these results, the Milan board of directors were adamant that Milan reach the fourth place in the league at the end of the season but Maldini failed and the team ended 6th.

2001-2002

Milan started their 2001-02 campaign by signing more star players including Javi Moreno and Cosmin Contra who took Deportivo Alavés to the final round of the UEFA Cup. They also signed Kakha Kaladze (from Dynamo Kyiv), Rui Costa (from AC Fiorentina), Filippo Inzaghi (from Juventus), Martin Laursen (from Hellas Verona), Jon Dahl Tomasson (from Feyenoord), Umit Davala (from Galatasaray) and Andrea Pirlo (from Inter Milan). Fatih Terim was appointed manager, replacing Cesare Maldini, and had moderate success. However, after five months in the club, Milan was nowhere near the top five in the league and Terim was sacked for failing to meet the board of directors' expectations. He was replaced by Carlo Ancelotti, despite rumours that Franco Baresi would be the new manager. Despite the injury problems of full-back Paolo Maldini, Ancelotti was successful and ended the Season 2001-02 in fourth, earing a place in the Champions League. Milan's starting line at that point was Christian Abbiati; Cosmin Contra, Alessandro Costacurta, Martin Laursen, Kakha Kaladze; Gennaro Gattuso, Demetrio Albertini, Serginho; Manuel Rui Costa; Andriy Shevchenko, Filippo Inzaghi.