Bob Ryland began playing tennis at the age of 9. He learned the sport from his father and Mary Ann “Mother” Seames in Chicago. He quickly gained popularity by winning the Illinois state high school championship in 1939 where he defeated Jimmy Evert, Chris Evert’s father. That same year, Ryland won the ATA Boys 18-and-Under Singles Championship. Playing for Wayne State University, Ryland was the first Black man to play in the NCAA tournament. He advanced to the quarterfinals in 1946. Ryland finished his undergraduate education at Tennessee A&I—where he also played tennis—and earned a Bachelor of Science in Physical Education in 1955.

Ryland had an exceptional amateur tennis career, winning a number of championships. At the Detroit Public Parks integrated tournament in 1946, Ryland won the Men’s Singles Championship. He won the Los Angeles Industrial City Championship six years later. In 1954 and 1955 he won the ATA Men’s Singles Championships. In 1955 Ryland was nominated by the ATA to play in the U.S. Nationals at Forest Hills. Having not played on grass courts before and no longer being in his prime, Ryland was defeated in the first round.

Ryland became the first Black professional tennis player when he joined Jack March’s circuit. He played his first professional match in Cleveland, Ohio in 1959. Ryland began his coaching career in the 1960s. He first worked at the St. Albans Tennis Club in Washington, D.C. where he gave tennis lessons. Afterwards, Ryland moved to New York City where he spent many years coaching primarily at the Midtown Tennis Club. He coached prominent younger players such as Venus and Serena Williams, professional players including Leslie Allen, and celebrities such as Barbara Streisand. Ryland did not stop playing tennis during this time. In 1989, he and partner Hank Conway became the Senior Tennis Tournament Doubles Olympic Champions.

In 1991, Ryland was inducted into the Wayne State University Hall of Fame. In 2009, Ryland was inducted into the Black Tennis Hall of Fame.