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. South Coast Derby 4–1 win over Harry Redknapp's Southampton side, who were eventually relegated at the end of the season. During the 2005–06 season and after achieving only four wins from a total of 20 games as Portsmouth manager, Alain Perrin was sacked on 24 November 2005, exactly one year to the day since Harry Redknapp left Portsmouth. Harry Redknapp then made a surprise return to manage Portsmouth again after leaving relegated Southampton. In January 2006, Portsmouth were sold by Milan Mandarić and bought by businessman Alexandre Gaydamak. New signings included a quartet from Tottenham Hotspur, then record signing Benjani