Like many players of his era, the Harvard-educated Holcombe Ward cemented his place in tennis annals with an Intercollegiate Doubles title in 1899, U.S. National Championship titles in both singles and doubles, and championships in Davis Cup competition. Impressively, Ward won seven U.S. National Championships, one in singles in 1904 over William J. Clothier in three hard-fought sets, 10-8, 6-4, 9-7, and six in doubles – two separate three peats. The doubles titles were split with Dwight Davis, his collegiate doubles partner (1899, 1900, 1901) and Beals Wright (1904, 1905, 1906). Ward, along with Davis and Malcolm Whitman, comprised the original United States Davis Cup Team in 1900 that swept the British Isles 3-0 at the Longwood Cricket Club in Boston. Two years later, the Davis Cup was played at the Crescent Athletic Club in Brooklyn where the U.S. team defeated the British Isles, 3-2. Ward helped the U.S. to the Davis Cup finals in both 1905 and 1906.
Ward took his game across the pond, competing in doubles at Wimbledon in 1901 (finalist) and 1905 (semifinalist) and a sole singles appearance in 1905, where he lost in the first round. The right-handed Ward is widely credited with originating the twist serve, a skill that helped rank among the U.S. Top 10 for seven of the ten years he competed. After he left the game, Ward turned his full attention to the administrative side of the game, serving as President of the United States Lawn Tennis Association (USLTA) from 1937-47.