Portsmouth F.C. European match was a 2–0 victory over Vitória de Guimarães in the first round on 18 September. Portsmouth went on to win the tie 4–2 on aggregate, progressing to the group stage. On 25 October 2008, Redknapp suddenly left Portsmouth for a second time, leaving his assistant Tony Adams to be promoted to the managerial role. On 27 November 2008, Portsmouth drew 2–2 with Milan, going 2–0 up through goals from Younès Kaboul and Nwankwo Kanu, but conceding two goals later in the game. Adams was dismissed in February 2009. Youth team coach Paul Hart took over as manager until
Portsmouth F.C. on leave and replaced by Portsmouth player, Steve Claridge in a player-manager role. On 23 February 2001, Graham Rix took over from Claridge. Portsmouth escaped relegation on the last day of the 2000–01 season when they won their final game and Huddersfield Town lost theirs, keeping Portsmouth up at their expense. During the summer break, former West Ham United manager Harry Redknapp was appointed director of football by Mandaric. A week before the new season began, 25-year-old Portsmouth goalkeeper Aaron Flahavan was killed in a car crash near Bournemouth on 5 August 2001. In a mark of respect, Portsmouth F.C.