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. was confirmed that Michael Appleton would leave Portsmouth to become the manager of Blackpool, along with first-team coach Ashley Westwood. The club confirmed that Guy Whittingham would take over as caretaker manager. On 9 November, Chanrai halted his attempt to buy the club. Six days later, PST signed an initial conditional agreement with PFK to buy the club. The Pompey Supporters Trust became the new owners of the club on 10 April 2013 after the club exited administration, with the parent company now officially named as Portsmouth Community Football Club Limited. On the pitch, Portsmouth went on to be relegated