Robertson began playing football with Deeside Boys Club before he started his football career by signing an "s" form with local club Aberdeen, where he won the Scottish Youth Cup alongside Joe Miller, Paul Wright and Stevie Gray. After becoming a first team regular aged 17, he won a Scottish League Cupwinner's medal against Rangers in 1989 and a Scottish Cup winner's medal in 1990 against Celtic in a match which ended with a thrilling penalty shoot out. Robertson moved to Rangers for £970,000 in 1991. With the Ibrox club, he helped the club to the last six of their joint-record nine championship titles in a row, as well as adding three more Scottish Cups and three more League Cups to his collection. He only received one red card during his spell, for a brutal bodycheck on his friend Joe Miller in the opening minutes of the Old Firm 1992 Scottish Cup semi-final, which broke the Celtic winger's ribs. During his time at the Gers, he won three caps for Scotland. After exactly 250 games for Rangers, Robertson signed for Leeds United in 1997 for £500,000, but recurring injury problems curtailed his spell in England and he played only 26 league matches in four years at Elland Road. Robertson retired from football in 2001 but was back playing in 2002 when he was appointed player/assistant manager of Scottish Football League club Montrose. He scored his first and only goal for Montrose in a 3–2 defeat at Cowdenbeath in the Scottish League Cup. His playing career with Montrose was cut short, however, due to one of his Achilles tendons snapping during a match against Greenock Morton in the same year.
Coaching career
In September 2006, Robertson was appointed manager of Montrose but he resigned just four months later. He moved to Phoenix, Arizona and worked as a director of boy's coaching at the Sereno Soccer Club. Robertson was head coach of USL Pro club Phoenix FC in 2013.
Real Kashmir
In January 2017 Robertson was appointed as the head coach of Indian I-League 2nd Division side Real Kashmir. Under his tenure Real Kashmir won the promotion to Indian top flight football, thus becoming the first team from Kashmir to be promoted to the I-League. Robertson also signed his son Mason to play for the club.
Statistics
Managerial statistics
Honours
Player
;Aberdeen
Scottish Cup: 1989-90
Scottish League Cup: 1989-90
;Rangers
Scottish Premier Division : 1991-92, 1992-93, 1993-94, 1994-95, 1995-96, 1996-97