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
Paul Hart on the brink of administration, had the worst ever start by a Premier League team, losing their first seven league games. This run was finally ended when Portsmouth recorded a 1–0 win over Wolverhampton Wanderers at Molineux on 3 October 2009. On 24 November 2009, with only two Premier League wins in 13 games and three points adrift at the bottom of the table, Hart was sacked. He declined the offer of an alternative role as technical director responsible for players aged 18–21, and left the club. On 17 December 2009, Hart was appointed manager of Queens Park Rangers following