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 Groves (footballer) on loan by his replacement Nicky Law. He left Grimsby during the summer of 2004 and signed for York City as a player. In July 2006, he joined the coaching staff at Portsmouth. He was appointed as caretaker manager at Portsmouth alongside Ian Woan on 24 November 2009 after Paul Hart left the club, before the appointment of Avram Grant two days later on 26 November. In July 2010, Groves joined West Ham United as senior coach working under manager Avram Grant having previously worked under him at Portsmouth, but he parted company with the club on 24 June 2011