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 Portsmouth F.C. to Plymouth Argyle in the semi-final. In the 2016–17 EFL League Two season, Paul Cook's side secured promotion to League One with a 3–1 win away at Notts County on 17 April 2017. On 6 May, the final match of the season, Portsmouth topped the table (for the first time in the season) following the 6–1 home win against Cheltenham and were crowned champions of League Two. Paul Cook resigned on 31 May 2017 to join Wigan Athletic. Kenny Jackett was appointed the new manager on Friday 2 June 2017. In May the Pompey Supporters' Trust (PST) voted in favour