Tiger Woods' Rival Still Holding Onto One ‘Regret’ 21 Years After Handing Team USA Humbling Loss - FOGOLF

“We’ve got an opportunity tomorrow, not just to win, but let’s try and win so well that we’ve already won the next one.” With those words, Colin Montgomerie had already set the tone in the European team room. In the corridors of Ryder Cup history, few moments resonate as vividly as the 2004 showdown at Oakland Hills Country Club. The European team produced a staggering 18½ to 9½ points victory over Tiger Woods’ United States, recording the largest margin of defeat for the Americans since 1981. At the heart of that triumph was Montgomerie himself, whose singles match against David Toms became one of the defining performances of the tournament.

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As Montgomerie stood over a five-foot putt on the 18th hole, the weight of the moment was palpable. A successful putt would not only secure his match but also contribute to Europe’s commanding lead. He later recalled, “I hold it just, just, it went in the side door.” However, it was his actions following the putt that have lingered in his memory. “Before I shook David Toms’ hand… I went and shook Bernhard Langer’s hand, gave him a hug, thanks,” Montgomerie admitted. “I’m not saying it saved my career, but to get picked was a big deal. And to hold a winning putt for him was a big deal.” Instead of first acknowledging his opponent, Montgomerie approached teammate Bernhard Langer, offering a hug and expressing gratitude.

While Montgomerie’s victory over Toms was a testament to his skill and resilience, it was his subsequent regret that humanized the moment. In the heat of competition, the handshake between opponents is a symbol of sportsmanship. Montgomerie’s decision to prioritize his celebration with Langer over acknowledging Toms was a rare misstep in his otherwise exemplary career.

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The 2004 Ryder Cup was a defining event in Montgomerie’s career. He acknowledges the emotional weight of the victory. The win came during a challenging period in his personal life, including the impending finalization of his divorce with his first wife, Eimear Wilson. The support of his teammates and the opportunity to focus on the Ryder Cup provided a sense of purpose and solace.

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However, the 2004 Ryder Cup wasn’t just Montgomerie’s crowning achievement; it reshaped the American side, influencing Tiger Woods’ approach to future Ryder Cups and redefining the narrative of his rivalry with Europe’s finest.

Tiger Woods’ reaction to the loss at the 2004 Ryder Cup

The tournament began with a high-profile ‘super pairing’ designed by U.S. captain Hal Sutton: Tiger Woods and Phil Mickelson were paired on Friday in an effort to dominate Europe’s top duo. The plan backfired. Constrained by golf ball rules and struggling chemistry, Woods and Mickelson lost both matches Friday, splitting a Saturday match but ultimately contributing to a European blowout. Teammate Fred Funk captured the mood of Woods after it was all over as he shared a ride with him and his then-wife, Elin.

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“I said, ‘How was it?’” Funk said. “And he goes, ‘How was what?’ I go ‘How was it?’ And he doesn’t reply. And I go, ‘Tiger, how was it with Phil?’ And he’s just shaking his head. I said, ‘What’s the deal?’ He goes, ‘He was useless! He didn’t help me one shot,” Funk continued. “And that was the year [Mickelson] just switched over to Callaway with all new equipment. He was never with us all week; he was always somewhere else, testing clubs, testing balls, trying to figure out. And [Tiger] just said, ‘He doesn’t know where the ball is going, he doesn’t know how far to hit it, he can’t keep it on the goal course, he didn’t help me one hole!’ … So we are just laughing.”

This candid display of frustration demonstrated Woods’ deep investment in the Ryder Cup and his realization that individual skill alone could not carry the team to victory. The 2004 Ryder Cup remains a pivotal intersection of personal triumph and collective reflection. Montgomerie’s winning putt symbolizes Europe’s precision, teamwork, and mental resilience, while his lingering regret reminds us of the human element: sportsmanship and respect beyond the scoreboard. For Woods, the loss was a humbling lesson in leadership and team cohesion, reshaping his approach to future Ryder Cups. He became more deliberate in mentoring teammates, fostering chemistry, and understanding the psychological dimensions of match play.