[3] Dwight won the first recorded tournament in the U.S. (and probably in the world, before the first Wimbledon Championships) played in August 1876 on the property of his uncle, William Appleton, at Nahant, Massachusetts.

After graduating from Harvard in 1874, he traveled in Europe, saw the new sport of lawn tennis being played, and brought the necessary equipment home.

Then he persuaded his uncle to mark out a court on his smooth front lawn so he could play a game with his cousin Fred Sears.

He never won the singles championship, but he reached the tournament final in 1883 losing to Richard Sears, with whom he did team to take five national doubles titles, from 1882 through 1884 and from 1886 through 1887.

In a rare transatlantic trip in those days, James Dwight entered the 1884 and 1885 Wimbledon tournaments, reaching the semifinals in 1885 (losing to Herbert Lawford).