Having won the Scudetto in the previous season, the Rossoneri began the 1999/2000 season with one of the most significant transfers of recent history: Andriy Shevchenko. Alongside the Ukrainian, Gennaro Gattuso, Diego De Ascentis, José Antonio Chamot, José Mari and Serginho all joined AC Milan. The first objective of the season was the Supercoppa Italiana Final against Parma, which the Gialloblù won with a 92nd minute winner from Boghossian. The league campaign was of a high standard again, but the Rossoneri weren't involved in the two-horse Scudetto race between Juventus and Lazio, in which the Biancocelesti were the eventual winners after the disappointment of the previous year. The Rossoneri ended the season in third, eleven points from first-placed Lazio, qualifying for the Champions League for the second season running. Shevchenko enjoyed a brilliant debut season for the Rossoneri, winning top scorer with 24 goals. Valuable proof of his abilities. The Coppa Italia journey ended in the quarter-finals after two legs against Inter.
The European season began with a goalless draw at Stamford Bridge against Chelsea, while the first match at San Siro saw Zaccheroni's side secure a 2-1 victory against Galatasaray, courtesy of goals from Leonardo and Shevchenko. However, the match on 21 September remained our only victory in the group stage, the last four games saw two draws at home (against Hertha Berlin and Chelsea) and two narrow away defeats, in Germany and Turkey. The latter, with Galatasaray mounting a late comeback, also cost us third place in the group and the possibility of relegation to the UEFA Cup.
