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
Joe Hart After a successful spell at Birmingham, Hart earned a place in the England squad for the 2010 FIFA World Cup in South Africa. Manchester City manager Roberto Mancini was unsure over the future of Hart and dispatched his goalkeeping coach, Massimo Battara to watch over him during his loan spell at Birmingham City. Battara reported that Hart was a "very good goalkeeper, with very high physical and technical abilities" and advised that he kept Hart in his plans for the years ahead. One of the major pre-season debates was whether Hart would start ahead of the experienced Shay Given after