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 F.C. (basketball) three pulled Kingston back to within a single point. Spaid made it 73-70 but Irish's fourth foul could not stop Kenny Scott, whose free-throw drew Kingston level with 4 minutes 20 seconds left. Paul Stimpson then gave Kingston a 73-75 lead before Alan Cunningham took over, sinking four consecutive free-throws then stealing the ball and racing away for a lay-up to put Portsmouth 79-75 clear with 2 minutes 39 seconds remaining. Colin McNish made one from the line and Dan Davis laid up to bring Kingston back to 79-78, then Rich Strong sank a pair of free-throws to edge Portsmouth