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. largely paid for the new North Stand, was present at the game, as captain of the visiting Aston Villa team! The new North Stand briefly held the nickname of "The Jimmy Allen Stand" for a while afterwards. Portsmouth ended the 1935–36 season in tenth place. Having established themselves in the top flight, the 1938–39 season saw Portsmouth reach the FA Cup Final for the third time with manager Jack Tinn, who had worn his 'lucky' spats throughout the qualifying rounds. This was indeed third time lucky, as Portsmouth managed to defeat favourites Wolverhampton Wanderers 4–1 in what the press had