Kyle failed to score on a regular basis at Coventry, and fared no better under his old Sunderland boss Mick McCarthy during a short loan spell at Wolverhampton Wanderers. In October 2008, Danny Wilson gave Kyle the chance to return to the north-east by offering him a short term loan at Pools.
Having made an encouraging start to his Pools career, with three headed goals in his first three home games, Kyle struggled to win the fans over, not helped by stories that Pools were paying a considerable amount of money for his services. Like Richard Barker and Jon Daly before him, Kyle found himself used as an easy long-ball option for the defence and this approach was unpopular with fans who had started the season looking forward to seeing more of the promising strikeforce of Joel Porter and James Brown. Kyle`s arrival saw Brown return to the right of midfield before a knee injury ended the young striker`s season in November. Kyle left Pools a month later at the end of his loan spell, having scored five goals in 15 starts.