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 later became caretaker manager, a day after the sacking of manager Shaun Derry on 23 March 2015, following a run of three wins in 24 league games. Hart guided the club to three draws in three games, before the appointment of Ricardo Moniz as manager on 7 April 2015. He subsequently left Notts County, stating it was always his attention to leave after the departure of Shaun Derry. On 29 August 2015, it was announced that Hart would return to Leeds United as the Academy Director and Under-21s Manager. He left the club on 1 April 2016 due to personal