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. a transfer embargo, meaning the club were not allowed to sign any players. Avram Grant took over at Portsmouth on 26 November 2009, replacing Hart, who had been sacked by the board two days previously due to the club's position at the bottom of the league table. In December 2009, it was announced that the club had failed to pay the players for the second consecutive month, and on the 31st it was announced player's wages would again be paid late, on 5 January 2010. According to common football contracts, the players then had the right to terminate their contracts