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
History of Portsmouth F.C. Hartlepool United in his first game, but the permanent job was given to Ritchie Barker, who took over a Portsmouth side in 17th place on 9 December. However, Portsmouth's form worsend under Barker and on 27 March 2014, he was sacked after just 20 games with the team just two points above the relegation zone. Awford once again stepped in as caretaker manager to be in charge of what was billed as "seven cup finals" to save the club. Portsmouth won five of them in a row and drew the other two, finishing 13th. Andy Awford's impressive run of results