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
Paul Hart on 14 February 2009. Hart continued as caretaker manager until the end of the 2008–09 season, Portsmouth executive chairman Peter Storrie announcing in March 2009, after a close 1–0 defeat to Chelsea, "(Alexandre Gaydamak) and I have been delighted with how the team have fared. They both have so much experience in the game and they have the respect of the players. We will review the managerial situation again at the end of the season." Hart was appointed as permanent manager on a two-year contract on 21 July 2009. In the 2009–10 season, however, Portsmouth, a club in turmoil and