Things began to change in 1992. Agassi had ended his boycott of Wimbledon in 1991, and he reportedly found the grass difficult to play on. In 1992, he began training with Wimbledon legend John McEnroe to overcome this handicap, and his hard work paid off when he beat Boris Becker and McEnroe himself to make it to the Wimbledon finals, against Goran Ivanisevic, a player famed for his hard serve. After losing the first match, Agassi came back to defeat Ivanisevic in the next two matches, but lost the next match. This time, Agassi did not choke. Instead, he went on to win in a hard-fought final match by a 6-4 score. In his excitement, he fell to his knees and screamed with joy.
By winning Wimbledon, Agassi had put to rest the myth that he could not win the big ones. But it was not all smooth sailing. The next year, bronchitis and a sprained wrist caused him to skip the Australian and French Opens. Still bothered by his wrist injury, and out of shape, he lost his Wimbledon title to Pete Sampras in the quarterfinals. Perhaps the highlight of that tournament was when Barbra Streisand showed up in the stands to support Agassi. For a time there was speculation of a romantic involvement, but neither party has confirmed them, and at the time Agassi was still very much with his long-time girlfriend Wendy Stewart.
In late 1993, Agassi's mentor and coach, Nick Bollittieri, announced that he was leaving to pursue other interests, a move that hurt him and may have contributed to his first-round loss in the U.S. Open a short time later. Agassi then missed the 1994 Australian Open, complaining of the same wrist injury that had troubled him at Wimbledon. Again, it seemed that he might be on his way out.