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. basis with a one-year contract. Portsmouth sold over 10,000 season tickets for the 2013–14 season, a record for any League Two club. In November 2013, Whittingham was sacked and a month later ex-Crawley Town manager Richie Barker was appointed Portsmouth boss, along with Steve Coppell as the director of football. Barker was sacked after 20 games in charge, with the club in serious danger of relegation to the Football Conference, and Andy Awford was again made caretaker manager. He won five games out of five played, guaranteeing Pompey's survival in League Two. On 1 May 2014, Awford was appointed Pompey's