Winning a major championship is the ultimate dream for every professional golfer. These 4 golf major championships — The Masters, U.S. Open, The Open Championship, and PGA Championship — define careers, shape legacies, and immortalize champions. But for every triumphant victory, there is often a devastating loss. Some defeats are so painful that they become part of golf folklore, remembered just as vividly as the wins themselves.

The Majors: Top 10 Toughest Losses looks back at the most heartbreaking moments in major championship history — losses that happened on the final hole, in playoffs, or through sudden collapses under unimaginable pressure. These moments didn’t just cost trophies; they altered careers, haunted players, and changed how fans remember the game.

How We Ranked These Losses

Not every defeat is equal. To rank the toughest losses in the 4 golf major championships, several factors were carefully considered.
First was how close the player came to winning — final-hole collapses, playoff defeats, or losses by a single shot naturally carry more emotional weight. Second was the stakes involved, such as whether the player was chasing their first major, a career-defining win, or even a Grand Slam. Third was how the loss occurred, with self-inflicted mistakes often hurting more than being outplayed. Finally, we considered legacy impact, meaning how strongly the moment defined the golfer’s career in the years that followed.
These criteria help explain why some losses in the 4 golf major championships still sting decades later.

Top 10 Toughest Losses at a Glance

Before diving deeper, here’s a quick overview of the most heartbreaking major losses:

• Jean van de Velde — 1999 Open Championship

• Greg Norman — 1996 Masters

• Phil Mickelson — 2006 U.S. Open

• Jordan Spieth — 2016 Masters

• Tom Watson — 2009 Open Championship

• Rory McIlroy — 2011 Masters (early collapse)

• Roberto De Vicenzo — 1968 Masters

• Colin Montgomerie — 2006 U.S. Open

• Adam Scott — 2012 Open Championship

• Doug Sanders — 1970 Open Championship
  
  

Each of these moments represents a unique kind of heartbreak — some sudden, some slow, but all unforgettable.

Top 10 Toughest Losses in Major Championship History

1. Jean van de Velde — 1999 Open Championship (Carnoustie)

No major collapse is more famous than Jean van de Velde’s final hole at Carnoustie. Standing on the 18th tee with a three-shot lead, van de Velde needed only a double bogey to win The Open Championship. What followed was pure chaos. A wild tee shot, a failed attempt over water, a visit into the burn, and a shocking triple bogey forced a playoff — which he then lost. The image of van de Velde standing shoeless in the water remains one of golf’s most haunting visuals. This loss didn’t just cost him a Claret Jug; it defined his entire career and is still referenced when discussing collapses in the 4 golf major championships.

2. Greg Norman — 1996 Masters Tournament

Greg Norman entered the final round at Augusta National with a six-shot lead, seemingly destined to finally win The Masters. Instead, it turned into one of the most painful Sundays in major history. Norman struggled from the opening holes, missing fairways and putts while Nick Faldo played flawless golf. By the back nine, the collapse was complete. Norman lost by five shots, and despite his greatness, this defeat became the defining moment of his career in the 4 golf major championships.

3. Phil Mickelson — 2006 U.S. Open (Winged Foot)

Phil Mickelson had never won the U.S. Open, and in 2006 he stood one hole away from finally lifting the trophy. A par on the 18th hole would have secured victory. Instead, Mickelson hit a disastrous tee shot, followed by aggressive decisions that led to a double bogey. He finished one shot behind the winner. In tears afterward, Mickelson admitted, “I am such an idiot,” a brutally honest moment that revealed how deeply the loss hurt — a pain felt in every discussion of the 4 golf major championships.

4. Jordan Spieth — 2016 Masters Tournament

Jordan Spieth arrived at Augusta as the defending champion and a heavy favorite. Everything unraveled on the par-3 12th hole. Holding the lead, Spieth hit two balls into Rae’s Creek, making a quadruple bogey that instantly erased his advantage. Though Spieth would later recover to win other majors, this Masters loss remains one of the most dramatic momentum swings ever seen in the 4 golf major championships.

5. Tom Watson — 2009 Open Championship (Turnberry)

At 59 years old, Tom Watson was one par away from completing one of the greatest stories in sports history. A simple par on the 72nd hole would have made him the oldest major champion ever. Instead, Watson bogeyed the hole and then lost the playoff to Stewart Cink. The disappointment was visible as Watson left the green, knowing he had been inches from immortality in the history of the 4 golf major championships.

6. Rory McIlroy — 2011 Masters Tournament

Rory McIlroy entered the final round with a four-shot lead and the world expecting greatness. But Augusta National can be unforgiving. McIlroy’s swing deserted him on the back nine, culminating in a shocking triple bogey on the 10th hole. His round of 80 sent him tumbling down the leaderboard. While McIlroy rebounded to win multiple majors later, this loss served as a painful lesson early in his career and remains a cautionary tale in the 4 golf major championships.

7. Roberto De Vicenzo — 1968 Masters Tournament

Roberto De Vicenzo lost The Masters without hitting a bad shot on Sunday. After signing an incorrect scorecard — mistakenly recording a par instead of a birdie — he unknowingly eliminated himself from a playoff. The error cost him a chance at a green jacket and became one of the most tragic administrative mistakes in sports history. De Vicenzo’s grace afterward only deepened the heartbreak remembered in discussions of the 4 golf major championships.

8. Colin Montgomerie — 2006 U.S. Open

Colin Montgomerie had multiple chances to win the 2006 U.S. Open but missed crucial putts on the final holes. A short par putt on the 18th would have forced a playoff; instead, it slid past the hole. Despite being one of Europe’s greatest players, Montgomerie never won a major. This loss is often cited as the closest he ever came to triumph in the 4 golf major championships.

9. Adam Scott — 2012 Open Championship

 Adam Scott held a four-shot lead with just four holes remaining at Royal Lytham & St Annes. What followed was a shocking collapse, including four consecutive bogeys. Scott watched as Ernie Els claimed victory, while his own hopes slipped away hole by hole. Though Scott later redeemed himself by winning The Masters, this Open Championship loss remains deeply painful in the context of the 4 golf major championships.

10. Doug Sanders — 1970 Open Championship

Doug Sanders missed a short putt on the final hole that would have won The Open Championship. He went on to lose the playoff to Jack Nicklaus. That missed putt haunted Sanders for the rest of his career and is often cited as one of the most agonizing moments in the 4 golf major championships.

Patterns Behind These Heartbreaking Losses

When reviewing the toughest losses in major championships, clear patterns emerge. Many occurred on iconic closing holes known for punishing mistakes. Others involved players chasing a first major or a career-defining victory. Pressure magnifies small errors. Poor decision-making, aggressive club selection, and emotional swings frequently played key roles. These moments show that the 4 golf major championships are not just tests of skill, but of mental resilience.

Iconic Shots and Holes That Defined Major Heartbreak

From Rae’s Creek at Augusta to the 18th hole at Carnoustie, certain holes have become symbols of heartbreak. These locations remind fans that majors often hinge on a single shot — one swing that can alter history forever.

Fan FAQs About Major Championship Losses

What is the biggest collapse in major history?
Jean van de Velde’s 1999 Open Championship collapse is widely considered the worst in the 4 golf major championships.

Which major loss hurt Greg Norman the most?
The 1996 Masters remains the most painful due to his large final-round lead.

Has anyone lost a major without playing badly?
Yes, Roberto De Vicenzo lost the 1968 Masters due to a scorecard error.

Do players recover from major heartbreaks?
Some do — like Adam Scott and Jordan Spieth — while others are forever defined by the loss.

Conclusion

Major championships deliver golf’s greatest triumphs — and its deepest heartbreaks. The Majors: Top 10 Toughest Losses remind us that the difference between glory and despair is often razor-thin. These moments continue to resonate because they reveal the human side of the game, where even legends are vulnerable under pressure. In golf, winning a major is unforgettable — but sometimes, losing one in the 4 golf major championships is just as enduring.