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 season, results and form were extremely indifferent. He was sacked on New Year's Day, 1991. Hart then moved into youth coaching firstly at Nottingham Forest, and then subsequently took charge of Leeds United's fledgling academy. Hart's proteges won the FA Youth Cup in 1993 and 1997 and formed the backbone of the Leeds side that reached the Champions League semi-finals in 2000–01. With International players such as Harry Kewell, Jonathan Woodgate, Ian Harte, Alan Smith, Gary Kelly, Paul Robinson, Matt Jones and Stephen McPhail. Hart then returned to take charge of Nottingham Forest's academy after a high-profile fall-out with Leeds