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 the club to become the manager of the England under-21 team. After less than a month of his tenure, Hart made his entire squad available for transfer, after being informed he had to drastically reduce the wage bill to avoid the club going into financial ruin. As a result, Hart lost several experienced and key players, notably Andy Johnson to West Bromwich Albion for £200,000, Alan Rogers to Leicester City for an undisclosed fee, and Stern John to Birmingham City for £100,000. During the 2002–03 season, with the financial problems alleviated somewhat, and having the benefit of a settled side,