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 Hart manager George Graham over the promise of Jonathan Woodgate. Forest's Under-19 side became immensely successful winning the Under-19 title in 1999–2000. As the first team were faltering, and the club spiralling further into debt, players such as David Prutton, Jermaine Jenas, Keith Foy, Chris Doig, David Freeman, Kevin Dawson, Gareth Williams, Richard Cooper and Gareth Edds were blooded, with a further line of players including Barry Roche, Andy Reid, Brian Cash, Eugen Bopp, John Thompson and Michael Dawson following subsequently. On 12 July 2001, Hart was promoted from Youth Academy Director to manager, succeeding David Platt, who had recently left