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
2009–10 Portsmouth F.C. season the season came in the 2009–10 FA Cup, in which they manage to advance to the final after beating Coventry, Sunderland, Southampton, Birmingham and Tottenham Hotspur in the semi-final. They played at Wembley Stadium in the final against Chelsea, a game that Chelsea won by 1–0. Portsmouth also participated in the League Cup and reached the quarter-finals. Manager Paul Hart was sacked in November and replaced by Avram Grant, who stayed until the end of the season. French striker Frédéric Piquionne scored eleven goals throughout the season and was the club's top goalscorer. The team kit is produced by Canterbury