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
Kenny Jackett and several trophies. He served as Millwall manager for six seasons, again bringing a promotion, before resigning in May 2013; weeks later he took over as manager of Wolverhampton Wanderers, a position he held until July 2016, yet again garnering a promotion along the way. Jackett was appointed Rotherham United manager in October 2016 before leaving in November. In June 2017 it was announced he would take over from Paul Cook to become the Portsmouth manager. The son of professional footballer Frank Jackett, who played for Watford between 1949 and 1953, Jackett joined his local club Watford at the age