In 1969 Gonzales's prevailed in the longest match ever played till that time, one so long and arduous that it resulted in the advent of tie break scoring. As a 41-year-old at Wimbledon, Gonzales met Charlie Pasarell, a Puerto Rican younger than Gonzales by 16 years.

Pasarell won a titanic first set, then with daylight fading, the 41-year-old Gonzales argued that the match should be suspended. The referee didn't relent, and thus the petulant Gonzales virtually threw the second set. At the break, the referee agreed the players should stop.

The next day, the serves, the volleys and all the prowess that made Gonzales a fiery competitor surfaced with trademark vengeance. Pasarell, seeking to exploit Gonzales's advanced years, tried to aim soft service returns at Gonzales's feet and tire him with frequent lobs. In the fifth set, Gonzales saved all seven match points that Pasarell had against him, twice coming back from 0–40 deficits, to walk off the court the eventual winner in a 5-hour, 12-minute epic.

The final score was an improbable 22–24, 1–6, 16–14, 6–3, 11–9. The match with Pasarell, however, is still remembered as one of the highlights in the history of tennis and has been called one of "The Ten Greatest Matches of the Open Era" in the November/December 2003 issue of TENNIS magazine.

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