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
History of Portsmouth F.C. proposed appointing another director in November, with responsibility for the youth set-up at the club. Redknapp disapproved of the proposal, but Mandarić pressed ahead and appointed Velimir Zajec. Redknapp, along with his assistant Jim Smith, subsequently resigned with immediate effect on 23 November. Zajec took over as manager, initially as caretaker, then on 20 December 2004 the club announced that he would manage the team for the remainder of the season. Their first game under Zajec was a 1–0 away win over Bolton in a hard-fought match where Portsmouth captain Arjan de Zeeuw and Bolton striker El Hadji Diouf had