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. permanent manager, signing a one-year contract. On a historic announcement on 29 September 2014, the club was able to declare itself debt-free after paying back all creditors and legacy payments to ex-players. The news came 18 months after the PST took control of the club. Following an unsuccessful EFL League Two 2014–15 campaign, Paul Cook was appointed new manager of Portsmouth on 12 May 2015. Paul Cook led Portsmouth to an EFL League Two play-off spot in the 2015–16 season after a 2–0 away win at Hartlepool United on 30 April 2016, but lost to Plymouth Argyle in the semi-final.