Winston Bennett is a retired American professional basketball player and former men's basketball coach. Bennett was selected by the Cleveland Cavaliers in the third round (64th overall) of the 1988 NBA Draft and went on to play three seasons in the NBA, mainly for the Cavaliers, from 1989 to 1992. His best year as a pro came during his rookie season with the Cavaliers when he appeared in 55 games and averaged 6.1 points per game.
A star at Louisville Male High School, Bennett was named "Mr. Basketball" for the State of Kentucky in 1983. He also earned ParadeMagazine All-American and McDonald's All-America honors, sharing MVP honors with Dwayne Washington. Bennett played collegiately at the University of Kentucky where he wore #25 and was known as "Steady Bee". As a freshman in 1983–84, Bennett appeared in 34 games for UK, averaging 6.5 points in 19 minutes per game as the Wildcats reached the Final Four, losing to Georgetown, 53-40.
Bennett married his wife Peggy, and has three daughters Princess, Jasmine and Stephanie, residing in Lone Oak, Kentucky.