The period of hard times (Tabarez to Terim)
1996-1997
Although successful in previous seasons, failed to transform Milan Zaccheroni such as The Dream Team first. In the next season, despite the emergence of Ukraine striker Andriy Shevchenko, Milan's disappointing their fans both in the 1999-2000 UEFA Champions League or Serie A. Milan out of Champions League early, only to win one of six matches (three draws and two loses) and end the 1999-2000 season in 3rd place. Milan does not become a challenge for the scudetto two competitors at the time, SS Lazio and Juventus.
In the following season, Milan qualify for the 2000-2001 UEFA Champions League after beating Dinamo Zagreb 9-1 aggregate. Milan started the Champions League with a high spirit, beat Besiktas JK from Turkey and Spanish giants FC Barcelona, which at that time consisted of world-class international superstars, Rivaldo and Patrick Kluivert. But Milan's performance began to decline seriously, the series against a team (which is seen as a small / weak technically to Milan), especially losing 2-1 by Juventus in Serie A and 1-0 to Leeds United. In the Champions League second round, Milan only won once and drawn four times. They failed to beat Deportivo de La Coruña of Spain in the final game and Zaccheroni fired. Cesare Maldini, father of team captain Paolo, elected and things get better soon. Maldini's official coaching debut in Milan starts with win 6-0 over U.S. Bari, who still have the young guns, Antonio Cassano. It was also under the leadership of Maldini that Milan derby defeat arch-rivals Internazionale with incredible score 6-0, a score that is never repeated and where Serginho starring in the game. However, after this peak shape, Milan started to lose again, including a disappointing 1-0 defeat to Vicenza Calcio, with the only goal in the match scored by a Luca Toni. Apart from this result, the board of directors insisted that Milan Milan reach fourth place in the league at the end of the season, but Maldini failed and the team ended up in sixth place.
Milan started the season 2000-2001 with the signing of the contract more star players including Cosmin Contra and Javi Moreno who took Deportivo Alavés UEFA Cup finals. They also signed a Kakha Kaladze (from Dynamo Kyiv), Rui Costa (from AC Fiorentina), Filippo Inzaghi (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 as manager, replacing Cesare Maldini, and quite successful. However, after five months at the club, Milan is not in the top five league and Terim was fired for failing to meet the expectations of directors.
After the departure of Fabio Capello in 1996, Oscar Washington Tabarez Milan recruit but hard struggle under his control was less successful, and they always lose in a few games early. In an attempt to regain past glory, they called back Arrigo Sacchi to replace Tabarez. Milan get a hard slap their worst defeat in Serie A, humiliated by Juventus FC in their own homes the San Siro with a score of 1-4. Milan buy some new players like Ibrahim Ba, Christophe Dugarry and Edgar Davids. Milan fought hard and end the 1996-1997 season ranked eleventh in Serie A.
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