During his career he rode for prominent owners such as Walter Jeffords, George Widener and William duPont Jr.

In 1936, Harry Richards rode Jeome Louchheim's colt Pompoon to victory in the richest and most prestigious race for juveniles, the Futurity Stakes at Belmont Park.

[3] Among his other top grade horses, Richards was the regular jockey for George Widener's future Hall of Fame inductee Eight Thirty on whom he won the 1939 Travers Stakes, the 1940 Suburban Handicap and in his final year as a jockey, the Metropolitan Handicap.

In 1940, Harry Richards was a founding member of the Jockeys' Guild and served as the organization's first president.

He and his wife Daisy were living in Solana Beach, California when he died at age seventy-two in January 1980.