 His first goal of the 2008 – 09 season came in Wigan's fourth game, a 5 – 0 victory against Hull City at the KC Stadium. He hinted in October 2008 that he would be interested in leaving Wigan to play in the Champions League, with former club Liverpool believed to be interested in signing him in the January transfer window. However, Wigan manager Steve Bruce hoped to persuade him to sign a new contract at the club. Heskey commented on reports of interest from Liverpool by saying "It would be lovely. We'll see how it goes." He scored his 100th goal in the Premier League against Portsmouth on 1 November 2008, which secured a 2 – 1 victory for Wigan. Dave Whelan, the Wigan chairman, hinted that Heskey could be transferred by Wigan in January 2009, as a fee would be received, whereas he would move on for free in the summer, which came after he had stalled on talks over a new contract. However, Bruce said he would only accept an offer for Heskey if it was "outrageous". He later said he was confident of keeping Heskey at the club. Heskey picked up a hamstring injury during a match against Bolton Wanderers in December 2008, which resulted in him missing an FA Cup third round tie against Tottenham. He later said he would stay at Wigan and see out his contract until the summer of 2009.
