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 Rushden & Diamonds F.C. at Boston United, which resulted in manager Barry Hunter being told his contract would not be renewed at the end of the season. Paul Hart took over as manager on 23 May and during the close season signed former Gillingham defender Chris Hope, Leo Fortune-West, Glenn Wilson, Paul Watson and Jon Ashton. However, following a poor run of results, Hart left by mutual consent in mid-October, with goalkeeping coach Tony Godden becoming caretaker manager. Mid- and late-2006 saw a lot of changes at the club. In July Helen Thompson became chairman, in November the club was taken over by former