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
Paul Evans (football assistant manager) runner up in an Autoglass Trophy Final. In 1986, Neil Warnock went to Scarborough as Manager and he took Evans, his former goalkeeper at Burton Albion, with him as his Assistant Manager. Warnock and Evans arrived at Scarborough and quickly signed Cec Podd, Barry Gallagher and Paul Kendell from Halifax Town, Mike Brolly and Tommy Graham from Scunthorpe United, David Kaye from Chester City and Andy Harrison and Steve Richards from Kettering Town. Warnock also added Stuart Mell who was with Warnock and Evans at Burton Albion. The season started pretty average so Warnock signed Ian Bennyworth and Mitch Cook.