He turned professional in 1961, and made 44 league appearances over the next three seasons before being sold to Fourth Division side Torquay United in 1964.
He was also in charge of Wigan Athletic during the 1999–2000 season, narrowly missing out on promotion after the team were defeated in the 2000 Second Division play-off final.
He turned professional with the Maine Road side in July 1961 and made his debut against West Bromwich Albion in 1962.
After 240 league games and 7 goals, Benson moved to Bournemouth & Boscombe Athletic in October 1970 for a fee of £12,000,[4] and was appointed captain by manager John Bond.
In January 1979, Benson returned to Norwich City to act as youth team coach and scout, working under his former colleague from Bournemouth and Torquay, John Bond.
He was offered the job, but declined on the grounds of ill-health, Ray Mathias taking over instead, with Benson remaining in an advisory capacity.
In April 2001, Rioch was replaced by Steve Bruce and Benson's role changed to that of youth development officer.
A month later Bruce also left, and the consequent arrival as Paul Jewell resulted in Benson being given the title of Director of Football.
He later became general manager at Birmingham, but left on 2 June 2006 to rejoin Wigan Athletic, where his role was described as "a link between the playing and administrative sides" of the club.