Born in West Bromwich, Ross began his career as a trainee at Leeds United in 1999 but made no appearances for the club and joined Stockport County on a free transfer in April 2000.
[1] He made nine league appearances, scoring two goals, and had a loan spell at Bristol Rovers, in two and a half seasons at Stockport.
[1] He joined Macclesfield Town in January 2003, after initially failing to agree personal terms,[2] and was allowed to go to Conference National side Northwich Victoria on a one-month loan in September 2003 to get match practice.
[3] He made 14 appearances for Macclesfield Town without scoring,[1] but did not form part of manager Brian Horton's plans for the 2004–05 season and was placed on the transfer list in August 2004.
[12] He subsequently moved to Gibraltar to assist newly appointed Nathan Rooney at Bruno's Magpies, helping the club achieve European football for the first time.