Defoe joined Portsmouth in January 2008 for £7.5 million. He scored the equalising goal on his debut, a 1–1 draw at home to Chelsea. In March 2008, he was unable to play against Tottenham as the Premier League ruled that he was ineligible to do so as he was initially signed on loan in January 2008. In Portsmouth's match against Wigan Athletic the following week, he scored twice; in so doing, he became the first ever Portsmouth player to score in his first five home matches. Due to appearances in Tottenham's third and fourth round ties, Defoe found himself cup-tied for all the subsequent matches of Pompey's successful 2007–08 FA Cup campaign. This also meant that he missed out on playing in Spurs' League Cup final victory over Chelsea, however he still received his winners' medal, albeit 10 years later, in December 2018. Defoe ended 2007–08 with eight goals in 12 appearances for Portsmouth.