Winston Keithroy Matthew Benjamin (born 31 December 1964) is an Antiguan cricketer who played 21 Tests and 85 One Day Internationals for the West Indies. He made his Test debut against India at Delhi on the 1987–88 tour. 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.
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. Now he is a coach for a leeward island (Antigua) at the Clare Hall Secondary School.