Benson made his first-class debut as a left-handed opening batsman in 1980 and was virtually an "ever-present" in the Kent side for the next fifteen seasons scoring over 18,000 runs (48 centuries) for the county. He was Kent's third highest aggregate run scorer in the post-war era and his batting average of 40.27 was the fourth highest for a major batsman in Kent's history (after
Les Ames,
Frank Woolley and
Colin Cowdrey). He scored 1,000 runs in a season 12 times, with a best of 1,725 runs (average 44.23) in 1987. Benson played 268 One Day matches (5 centuries, 53 fifties, 6 "man of the match" awards) for Kent scoring 7814 runs at an average of 31.89. These included a
man of the match-winning century as Kent won a
NatWest Trophy semi final in 1984, although they lost in the final to
Middlesex. For the 1991 Benson was appointed captain of Kent and on his first day as captain he scored a career best 257 against
Hampshire. Under his captaincy Kent were runners-up in the
County Championship in
1992,
Sunday League champions in
1995 (runners up in
1993) and
Benson & Hedges Cup finalists in
1992 and
1995. At the end of the 1995 season Benson was forced to retire due to a knee injury. Overall, Benson scored a century every 10.23 innings, the third highest rate for Kent, including a century in each innings v Warwickshire in 1993. Benson and
Neil Taylor scored the highest opening partnership (300) for Kent v Derbyshire in 1991.
Brian Luckhurst named Benson as Kent's greatest post war opening batsmen and referred to him as "His generation's unsung hero." ==International playing career==