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. from the late 2012-13 EFL League One season after going 23 games without a win, however The Football League still agreed to deduct the ten points from Portsmouth for going into administration, despite them already being relegated. Portsmouth were tipped for promotion in the 2013-14 EFL League Two season by bookmakers, with Guy Whittingham given the first team job full-time but after a slow start to the season, Whittingham became increasingly unpopular. He was sacked on 25 November 2013 with Portsmouth just six points above the relegation zone. Andy Awford took the role of caretaker manager, earning a point against