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. won back-to-back consecutive top flight League titles since the end of World War II. In the following 1950–51 season, League champions Portsmouth finished in 7th position, 13 points behind title winners Tottenham Hotspur. The next 1951–52 season saw an improvement, with Portsmouth finishing in 4th place, 9 points behind title winners Manchester United. Eddie Lever took over at Pompey in 1952 after championship-winning manager Bob Jackson joined Hull City. In the 1952–53 season, Portsmouth finished in 15th place and only 4 points above the relegation zone, with Arsenal F.C. winning the league title. In the 1953–54 season, Portsmouth finishing in