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
The Wrestling Classic pitted Paul Orndorff against Bob Orton. Orton was disqualified after he hit Orndorff with his cast. The quarterfinals began with Adrian Adonis facing Dynamite Kid. During the match, Adonis accidentally hit his manager Jimmy Hart and collided with Hart. Dynamite took advantage and pinned Adonis to win the match. Ricky Steamboat then faced off against Randy Savage. The referee was distracted by Miss Elizabeth as Savage took advantage and pulled out brass knuckles from his tights and hit Steamboat before pinning him to win the match. Junkyard Dog then defeated Moondog Spot after a head butt. Strangely, there was no