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Craig is a versatile and experienced player who re-joined Cheltenham Town for a second spell in February 2008.

He began his career as a trainee at Nottingham Forest, where he played youth team football alongside current Cheltenham Town captain John Finnigan. In those days Craig was a central defender and he took part in the squad which won promotion to the Premiership in 1994. Craig played for Forest in the Premiership and also enjoyed loan spells with Burnley, Bristol Rovers, Gillingham and Watford.

Following a £750,000 move to Huddersfield Town in 1999, Craig began to play in both midfield and at left-back. He made over 100 appearances for the Terriers then joined Sheffield Wednesday for £100,000 in 2002.

His stay at Hillsborough was not a happy one, however, as the Owls suffered relegation to Coca-Cola League Two and Craig was a victim of cutbacks at the club. He was released after a loan spell with Grimsby Town and spent the latter part of season 2004-2005 with Bradford City.

Former Robins boss John Ward moved in to secure Craig's signature in July 2005, aiming to deploy his naturally left-footed ability wide in midfield. Immediately his presence in the squad paid dividends for a relatively young team. His versitility on the left hand side of the pitch made him stand out throughout the promotion winning campaign although he was unfortunate to suffer a painful injury early on in the Play-Off Final at Cardiff. Nevertheless, he fully recovered from his broken nose and his experience of football in League One, and beyond, enabled him to be a consistent performer during season 2006-07.

He began last season with Gillingham but left Priestfield Stadium mid-way through the campaign to return to Cheltenham Town. His versatility as either a defender or midfielder helped the Robins maintain their League One status.