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. following 2004–05 season in the Premiership, Harry Redknapp unexpectedly walked out on Portsmouth on 24 November 2004 after a row with chairman Milan Mandarić over the appointment of new Director of Football Velimir Zajec at the club. Shortly afterwards on 8 December 2004, Harry Redknapp was announced by Southampton F.C. chairman Rupert Lowe as their new manager, with Jim Smith as his assistant. Velimir Zajec then replaced Redknapp as Portsmouth manager, but in April 2005, Zajec was replaced by Frenchman Alain Perrin. Perrin managed to secure Portsmouth's Premiership status with a few games of the season left, including a milestone