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
Ian Woan July 2007, it was announced that Woan had joined Premier League outfit Portsmouth as coach of their Under-18s. In November 2009, he was appointed joint caretaker manager at Portsmouth along with Paul Groves, following the dismissal of Hart. His appointment only lasted several days, and he moved aside for the arrival of Avram Grant as the full-time manager. In the summer of 2010, following the departure of Grant to West Ham United and the appointment of Steve Cotterill as the new Portsmouth manager, Woan was appointed first team coach. In June 2011, he joined Watford as assistant manager. In the