Ryland broke through barriers of race and class by becoming the first African American to become a tennis professional. His success in both American Tennis Association (ATA) and integrated amateur tournaments around the country made him one of the best known Black players in the US.
Robert Ryland was the first African American professional tennis player, and the African American male tennis player to compete in the NCAA Championships. In 1946, Ryland reached the semifinals representing Wayne State University. Later, as a player-coach, he accomplished another first when he twice led Tennessee A&I (now Tennessee State University) to the small college national championships (1954 & 1955), before graduating from the HBCU with a Bachelor of Science degree. Prior to attending Wayne State and Tennessee A&I, Ryland attended Xavier University of Louisiana before leaving to serve the United States Army from 1941-45, during World War II.
Following his college career, Ryland won the 1955 American Tennis Association (ATA) National Championships and later qualified for the 1955 US National Championships. Ryland defended his ATA National Championship title in 1956 before officially joining the United States Lawn Tennis Association (USLTA) as a professional in 1957.
After retiring from the professional tour, Robert coached and taught tennis for over 60 years, advising some of the world's top-ranked professionals, including Venus and Serena Williams, Harold Solomon, Renee Blount, Leslie Allen, and Arthur Ashe. He also taught some of the government and entertainment industry’s elite, including Robert MacNamara, the Kennedy family, Barbra Streisand, Tony Bennett, Mike Wallace, and Eartha Kitt.