Harold Mahony was born to a wealthy barrister in Scotland, but lived much of his life in Ireland. His father had a tennis court built at their home at Dromore Castle in County Kerry, Ireland, where Mahony learned the game. He made his début at Wimbledon in 1890, losing in the first round. In 1891 he reached the semi-finals of the All-Comers Event, repeating that finish in 1892. In 1893 he made it to the All-Comers final, losing there to Joshua Pim. After losing in the second round in 1894, he skipped the 1895 event, but in 1896 came through to become Wimbledon Champion, defeating Wilfred Baddeley in the final, 6-2, 6-8, 5-7, 8-6, 6-3, the longest Wimbledon men’s final until 1954 when Jaroslav Drobný defeated Ken Rosewall. Mahony competed at Wimbledon through 1904, making the All-Comers final again in 1898, also winning the Irish title that year, but he never won another major. In 1905, Mahony went for a bicycle ride and never returned from it. His body and broken bike were found at the base of a steep hill near his County Kerry castle.