He began to play regularly towards the end of the 1988–89 season, alongside fellow homegrown youngsters Aidan Newhouse, Chris Lightfoot and Colin Woodthorpe.
He remained involved in first-team duties for the next two years but at the end of the 1990–91 season he opted to join Fourth Division club Maidstone United for an initial £30,000 along with teammate Neil Ellis.
[4] After less than a year at Maidstone, Painter returned north by joining Burnley for £25,000, helping them clinch the Fourth Division title.
[5] Painter's three-year stint at Feethams included an appearance at Wembley Stadium in the Division Three play–off final against Plymouth Argyle, where Darlington suffered a 1–0 defeat.
He spent three years at Spotland and then moved across the Pennines to Halifax Town, where he played his final Football League match against Darlington on 28 April 2001.