Lendward Simpson, Jr.
- 1964 defeated Dick Stockton to win the US Lawn Tennis Association's Eastern Boys 14's Championships singles title at Forest Hills
- Later the same year, became the youngest male player to ever play at the U.S. National Championships (now U.S. Open)
- First Person inducted into Cheshire Academy's athletic Hall of Fame
- Was the first African American player to compete in World Team Tennis, signing with the Detroit Loves