Harold retained his Top 32 ranking, and started the 2008–09 season ranked at #28, his highest ranking since 2003. In the first ranking event of the new season, the 2008 Northern Ireland Trophy, he beat Ricky Walden 5–2, Graeme Dott 5–3, Stephen Lee 5–4 and defending champion Stephen Maguire to reach the semi-finals, his first appearance at that stage of a ranking event for five years. He then moved into a 5–1 lead against John Higgins and won 6–4, to reach his first final since 1994, which he lost 9–3 to Ronnie O'Sullivan. Harold's performance in this tournament moved him up to 14th in the provisional world rankings. Harold remarked after the final that, aside from claiming the World Championship, his one other remaining ambition in the game is to score a victory over O'Sullivan, who he has never beaten in a ranking tournament. The 2008 Northern Ireland Trophy marked his tenth consecutive failure to do so.