Stolle is notable for being the only male player in history to have lost his first five Grand Slam singles finals, the fifth of which he led by two sets to love. However, Stolle went on to win two Grand Slam tournament singles titles, the 1965 French Championships and the 1966 US Championships. At Wimbledon and the Australian Championships he finished as runner-up in these tournaments and losing to compatriot Roy Emerson on no fewer than five occasions. Lance Tingay of "The Daily Telegraph" ranked Stolle as World No. 2 in 1966.