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
1999–2000 Portsmouth F.C. season 1999–2000 Portsmouth F.C. season During the 1999–2000 English football season, Portsmouth F.C. competed in the Football League First Division. Manager Alan Ball's contract was terminated on 9 December with Portsmouth in the relegation zone. He was replaced by Bristol City manager Tony Pulis, who steered the club to survival in the First Division. The end of the season saw the retirement of club goalkeeping legend Alan Knight, who made 801 career appearances over 22 years, all spent at Fratton Park. His final appearance came in a First Division match against Norwich City at Carrow Road in January. Portsmouth ended their