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 Stadium cost cutting exercises and Portsmouth suffered as a result despite the fact that the GRA had pledged a new state of the art Portsmouth stadium previously. Lee McAlpine replaced Dave Stow as Racing Manager before Eric Graham took over and in 1998 Jim Snowden left Catford Stadium to take over as General Manager from the retiring Bill Francis. During 2006 the tracks 'Inside Sumner' hare system was replaced by the 'Swaffham' In 2008 it was announced that Portsmouth City Council's long term lease was nearing its end and they were considering selling the site for redevelopment. Lease holders GRA offloaded