Lenny Simpson grew up around giants. Growing up in Wilmington, his neighbor was Dr. Hubert Eaton, the man who sponsored Althea Gibson. He also grew up around player Nathaniel Jackson. Encouraged by all three, eight-year-old Lendward began to practice tennis and was soon taken under the wings of Dr. Robert Walter Johnson, a prolific coach who introduced Black athletes to competitive tennis. Simpson won the US Lawn Tennis Association (USLTA)’s Eastern Boy’s 14s Championships at Forest Hills in 1964, and that same year he became the youngest player to play at the U.S. National Championships. He lost in the second round to friend and mentor Arthur Ashe.

Simpson attended school at Cheshire Academy in Connecticut and was the first individual to be inducted into the school’s athletic Hall of Fame. He continued to play throughout his collegiate career at East Tennessee State University. He was the captain of ETSU tennis team from 1968 to 1972 and coached the team in 1972 and 1973.

Simpson turned professional in 1973 and was the first Black player on a World TeamTennis franchise when he joined the Detroit Loves. He became a tennis instructor in 1977 and eventually settled in Tennessee, where he became co-owner of Center Court Racquet Club.

Currently, Simpson is the owner of Simpson & Associates, which organizes tennis exhibitions. In 2013, Simpson founded One Love: Lenny Simpson Tennis and Education Fund, an organization which provides education and tennis instruction to at-risk youth. In 2019, One Love began working on making the home of Dr. Hubert A. Eaton, a historical site. Restoration of his backyard tennis court at 1406 Orange Street in Wilmington, North Carolina was completed in December 2020.

In 2014, Simpson was inducted into the Black Tennis Hall of Fame.