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
History of Portsmouth F.C. and manage the £70 million debt. This came to a head when Septembers wages were not paid on time, whereupon the club was once again taken over, this time by Saudi Arabian businessman Ali Al-Faraj. By this time, the team were, as expected, languishing at the bottom of the table, and Avram Grant was brought in as director of football. As poor results continued, however, Paul Hart was sacked and Grant took over as manager. Al-Faraj, however, did not seem to bring what was promised; he never attended Portsmouth matches and again club wages were not paid on time for