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 was to keep them in the Championship. This was achieved on Hart's final day in the job after a 2–2 draw with Sheffield Wednesday, which saw the hosts relegated instead. Hart left Crystal Palace at the end of the season. In June 2010, it was announced that Hart was on the shortlist to become the successor to Phil Brown at the recently relegated Hull City. The job however was given to Leicester City manager Nigel Pearson. Hart was appointed manager of Swindon Town on 3 March 2011, with his new club in the League One relegation zone. He appointed former