Career
Hennessey was ranked among the 10 best American players three times, his highest ranking being Number. 4 in 1928. In both 1927 and 1928 he was the World Number. 8 ranked player by A Wallis Myers.
In 1925 he and Ray Casey reached the finals of the Wimbledon doubles.
In an era in which tournament doubles matches were considered almost as important as singles, they lost one of the most famous matches in the early history of tennis, being beaten 4–6, 9–11, 6–4, 6–1, 3–6 by one of the great French teams of Jean Borotra and René Lacoste. Hennessey reached the quarterfinals of the 1927 United States. National championship and the quarterfinals at Wimbledon in both 1925 and 1928.
A July 14, 1924 Time Magazine article called him The Indianapolis Cyclone. Also in 1927, he was runner-up at the Illinois State championship, losing in a five-set final to Bill Tilden.
In 1984 Hennessey was one of the first four inductees into the USTA/Midwest Section Hall of Fame.
There is an annual John F. Hennessey Open tournament in Indianapolis for junior players. Doubles
= Titles = Finals =.