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 Guildhall "Nelson", "Victory", "John Pounds" and "Harry Redknapp" in a 2008 public poll by Portsmouth City Council in 2008. The official naming was stalled due to the high popularity of internet votes for Harry Redknapp's name from unregistered anonymous voters. Redknapp, the former Portsmouth Football Club manager had suddenly departed the club for Tottenham Hotspur F.C. shortly before bell name voting commenced, which had left a wide range of emotions among many Portsmouth Football Club fans and city residents. Foul play, possibly from rival football supporters was suspected by Portsmouth City Council, who had organised the vote, and the four quarter