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
2009–10 Portsmouth F.C. season the Premier League placed the club under a transfer embargo, meaning the club were not allowed to sign any players. Paul Hart was sacked by the board on 24 November 2009, based on the poor results that left Portsmouth at the bottom of the league. He was offered the role of technical director responsible for players aged 18–21, but he declined. Coaches Paul Groves and Ian Woan took temporary charge of the team. On 26 November 2009, Portsmouth F.C. announced on its official website that Avram Grant had been appointed as manager. On 3 December 2009, it was announced that