Harold Simpkins was from the Yarmouth Country Club on Cape Cod in Massachusetts. Simpkins did not qualify for match play at the 1904 Olympics, but made it to the second flight of the consolation events, where he lost in the semi-finals to Fred Semple. Simpkins attended the St. Paul’s School in Concord, New Hampshire, and then Harvard College, graduating in 1907. In 1907 he joined the Hydraulic Press Brick Company in St. Louis until 1914, when he transferred to the same company’s office in Dubois, Pennsylvania, where he managed the company.