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
Portsmouth F.C. Drogba. Despite being the FA Cup finalists, the club were denied a licence to play European football the following season in the UEFA Europa League. In May, Grant resigned as Portsmouth manager. On 17 June, the club's creditors voted for a company voluntary arrangement (CVA), with an 81.3% majority; HMRC, Paul Hart and the agent of Portsmouth midfielder Tommy Smith were the only ones to reject it, but HMRC appealed against the CVA due to the reduction of its considerable debt. On 15 July 2010, HMRC appealed against the proposed CVA on the last day before it would be formally