Paul Gleeson played only doubles at the 1904 Olympics, losing in the first round with German Hugo Hardy, the only foreign player in the 1904 tennis competition. A St. Louis native, Gleeson was a member of the St. Louis Amateur Athletic Association (AAA). He continued to play local tournaments over the next few years. In 1908 he and Yale player Drummond Jones won the Central States doubles championship, with Gleeson losing in the final of the singles. In 1909 Gleeson switched to playing doubles at that event with Orion Vernon, and they lost in the final to Jones and Charles S. Peters.