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Did you know about Tiger Woods‘s tragic loss during a playoff? Most of the golf world knows about the exceptional career and wins of the greatest of all time. However, Woods losing against the home crowd that too in the playoff was the untold story hidden behind the impressive career record of the golfer.

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Tiger Woods has won the most PGA Tour events, with 82 victories, including 15 major events. However, there was only one golfer who has achieved to beat the greatest in a playoff. It was Billy Mayfair, who won 5 times on the PGA Tour. Out of the five, the 1998 Nissan Open is a special one for him as well.

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In the recent podcast of The Sweet Spot, Mayfair joined in as a guest. And without any doubt, the question of his being asked about his win against the 15-time major winner was obvious. He was asked, “How the hell did you do that? Walk us through the whole thing.” Mayfair answered by sharing that he participated in the event because of his wife. He Shared about his performance a week before the Nissan Open, where he finished runner-up and wasn’t really sure to participate. However, his wife pushed him to participate and with the event taking place at Valencia instead of the usual Riviera, he went on to give it a try.

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Further sharing about his performance at the event, he expressed his joy when he was putting great since the beginning. “I think I had a six-shot lead after two days,” Mayfair added. Tiger Woods, who grew up in that area, had fans’s support which the 5X PGA Tour winner pointed out. Woods, being two groups ahead of Mayfair, had already made a birdie at the 18th hole, which made it clear for the golfer to make a birdie, which he did to make it to the playoff.

For the playoff situation, he shared, “Everyone thought Tiger would win this.” As the playoff began at the par-5 hole. Sharing further, he said how his shot went to the same spot from where 30 minutes ago he shot. “I don’t know he walked around like 20 minutes it felt like. I think he wanted me to think about it. But he hit a great putt, just missed over the top edge of the hole and you know, of course, he went onto his knees.”

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This provided Mayfair the opportunity to take away the championship. He was saying to himself, “It’s inside left, inside left.” Finally, the shot went in as planned, and it was the greatest moment for the golfer to beat Tiger Woods.

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While in his career, it was the first time when fans witnessed a tragic loss for Woods. But the unfortunate thing happened yet again at the last event of the 2024 schedule.

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Tiger Woods’s second unfortunate loss in a playoff

Unlikely for the fans, at the last event of the 2024 calendar year, the PNC Championship which Tiger Woods featured with his son Charlie Woods, saw an unforeseen defeat. Team Woods were trying for their first win at the event, but it seemed that team Langer would not let that happen this year.

With both teams going neck to neck, the scores after the 36-hole were tied at 59 and 57 in the two rounds. While for the tie, the team went on to play in the playoffs, where the exceptional eagle putt from Bernard Langer snatched the first victory from the Woods team. Langer has won the event six times, 2 titles with Stefan Langer and the remaining 4 with Jason Langer.

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The defeat of the greatest is a rare sight but has been in the books of history. Even for the players, it is an achievement to beat him in the playoffs. Did you know about Woods’s loss at the 1998 Nissan Open? Share your thoughts with us in the comments below.

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Tanmay Sharma

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Tanmay Sharma is a Golf Journalist at EssentiallySports, where he has already penned more than 650 stories across the Live News and Trends desks. A graduate in Communication from Bennett University (Times Group), he brings a newsroom-honed precision to his live weekend coverage of golf’s biggest stages. Tanmay played an instrumental role in shaping ES’ digital-first golf section, balancing real-time leaderboard updates with a thoughtful lens on what those moments mean in the sport’s broader arc. An eight-year veteran of the content and media industry, Tanmay has worked across journalism, marketing, and editorial strategy, sharpening a versatility that now powers his golf storytelling. A lifelong golf fan, he thrives on digging into the untold, off-course narratives that reveal the human side of the game, stories of grind, setbacks, and resilience that numbers on a scorecard can’t capture. Whether in the heat of a major Sunday finish or while chronicling the rise of tomorrow’s stars, Tanmay connects fans to the heartbeat of golf with clarity and empathy.

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Ridhiman Das

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