Winston Keithroy Matthew Benjamin (born 31 December 1964) is a former Antiguan cricketer who played 21 Tests and 85 One Day Internationals for the West Indies.
After eight Tests he was left out of the team until 1993, when he played consistently for two years, but he was dropped again after Australia's 1994–95 tour and never returned to the side.
Benjamin took 39 wickets at an average of 19.30 in his first 11 Tests, though his final ten appearances yielded 22 scalps at 40.68.
He played more regularly in the shorter format of the game, and was a fixture in the side from his debut against Pakistan at Peshawar in 1986–87 until West Indies' 1995 tour of England.
After his playing career at the highest level was over, he acted as coach for the Leeward Islands, but was sacked in June 2005.