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-pointer on the buzzer to narrow their margin of victory to 88-85. Shackleford scored another 33 at Manchester Giants, who beat Portsmouth 80-73, before the curtain came down at home to Birmingham Bullets on 10 March. A fourth future Portsmouth player, Karl Tatham, appeared against them, scoring 12 points, but the day was all about whether the departing players could record a second victory to say farewell. At half-time it was a possibility, with Portsmouth only down 42-36, but Birmingham extended their lead to 21 points before a late home surge took the final score to 86-79 in the visitors'