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. retired his number 1 shirt for the season. Portsmouth signed veteran Croatian playmaker Robert Prosinečki on a one-year deal and Peter Crouch for the start of the 2001–02 season. Rix lost his job on 25 March 2002, with Harry Redknapp taking over. Former Portsmouth manager Jim Smith was asked to team up with Redknapp, and while he initially turned the offer down to remain as assistant at Coventry City, he soon arrived at Portsmouth after a change of manager at Coventry saw almost all of the club's coaching staff being dismissed. Peter Crouch scored 19 goals for Portsmouth, but was