Andre Agassi's ex-coach throws light on their first dinner conversation: "I can't believe you freaking lost to me"

Andre Agassi's former coach Brad Gilbert recently shared how their partnership began. Gilbert, who recorded four victories against Agassi, found it "shocking," as he understood the American's game well and believed those losses were avoidable.

During the Tennis Channel's Inside-In podcast, Gilbert was asked what led him into coaching in his early 30s. He began coaching Andre Agassi in 1994 which was before Gilbert had officially retired in 1995.

The 63-year-old explained that he had a great understanding of the game during his playing career. Gilbert believed Agassi's four losses against him were avoidable and helped the latter increase his efficiency through coaching.

"When I went to dinner with Andre and we were starting to talk about where his tennis was at and where it could go, the first thing was, I can't believe you freaking lost to me four times," Gilbert began (at 14:38).

Gilbert and Agassi faced each other eight times during their playing careers and they were tied at 4-4.

"I mean, that's shocking in itself that you've lost to me four times. And I feel like just from playing you, I have a better understanding of how you can become a better player. There's no way you should lose to me because it was, you know, a lot of times he would lose to himself, losing to me," Gilbert continued.

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Brad Gilbert opens up about Andre Agassi's "incredible" 26-match winning streak in 1995

Andre Agassi (L) and coach Brad Gilbert in1996 (Image: Getty)

Andre Agassi had an outstanding 1995 season, securing his first Australian Open title and dominating the summer hardcourt events by winning Masters 1000 titles in Cincinnati, Miami and Florida.

Heading into the US Open as both the defending champion and top seed, Agassi defeated top players to reach the final. His unbeaten streak extended to 26 matches before he lost the US Open final to Pete Sampras 4-6, 3-6, 6-4, 5-7.

When asked about the streak, Gilbert, during his appearance on Tennis Channel's podcast said:

"It was incredible. It's probably not on the pantheon like it should be because he won 26 in a row and didn’t win the 27th," Gilbert said. [15:35]

"The ability to go from a player who made tons of winners and tons of unforced error, to a player who just played unbelievably solid and he would beat you with that, it was a beautiful thing to see," he added. [16:10]

Notably, in a 2009 interview, Agassi reflected on how the loss to Sampras left him feeling like a "loser," despite his success. He shared that the defeat triggered a deep depression, leading to a sense of emotional detachment and making him realize just how "miserable" tennis had made him feel at the time.