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. Second Division season, gaining a new club record 9–1 Fratton Park home win over Notts County along the way, which is still the highest home win scoring record to date. Portsmouth's promotion to the top division in English football was a double celebration; the first achieved by a football club based south of London, and the first achieved by a club graduating from the Third Division to the First Division. South Shields manager Jack Tinn joined Portsmouth as new manager on 1 May 1927, replacing John McCartney who had resigned due to ill health. Portsmouth's debut season in the 1927-28