[2] After his mother and twin brother died of pneumonia when he was a baby,[3] his father Robert sent him to live with his grandmother in Mobile, Alabama where he helped his great-grandfather pick cotton.

[3] Ryland attended Tilden Tech High School in Chicago, and while a student there won both the Illinois State and junior ATA singles titles.

[4] After leaving Xavier, Ryland served in the U.S. Army from 1941 to 1945[3] and after an honorable discharge, received another tennis scholarship to Wayne State University in Detroit, playing there for two years.

[7] Ryland also broke another barrier at the Los Angeles Tennis Club,[3] when he played and lost to Ham Richardson in the Pacific Southwest Championships, 6–4 and 7–5.

[7] After leaving Tennessee, Ryland moved back east and became the physical education director of the YMCA in Montclair, New Jersey,[7] but left there in 1957 to teach tennis in New York.

[12] In addition to coaching professionals, Ryland also taught several celebrities, including; Barbra Streisand,[10] Bill Cosby,[6] Tony Bennett,[10] Mike Wallace,[3] Eartha Kitt,[3] Dustin Hoffman,[13] David Dinkins[12] and Mary McFadden.