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
Portsmouth F.C. after a string of bad results. Burrows was replaced by coach Graham Paddon until the end of the season, finishing in 17th position. Jim Smith's arrival as manager at the start of the 1991–92 season sparked a revival in the team's fortunes and that year Portsmouth reached the semi-finals of the FA Cup, meeting Liverpool at neutral ground Highbury on 5 April 1992 – the 94th Anniversary of Portsmouth Football Club. Portsmouth took the lead in extra time from a 111th minute Darren Anderton goal. However, Liverpool's Ronnie Whelan equalised five minutes later, and the semi-final match ended tied 1–1