Golf’s oldest major has always provided the fans with the most memorable and gut-wrenching moments of the century. With a history that surpasses 152 years, The Open Championship has been the most sought-after title, which has broken many hearts in the golf world. After all, not everyone had been fortunate enough to lift the Claret Jug, the highly coveted trophy that replaced the Challenge Belt.

While Tom Watson and Jack Nicklaus’s ‘The Duel in the Sun’ remains one of the best finishes to the Open Championship, there are a few that left the pros empty-handed or teary-eyed at the end of the 18-hole rollercoaster.

5. Constantino Rocca’s brilliant performance yet eventual loss

In the 1995 Open Championship, John Daly had finished his final round 1 under 71 at the St. Andrew Old Course and was chain smoking while watching Constantino Rocca play the final hole. The Italian pro needed a birdie to tie with Daly and force a playoff. But while playing the 18th hole, Rocca’s hands were trembling.

He took the first shot, and his ball ended up in the Valley of Sin. There were no expectations of recovery, and Rocca was to lose it all. However, from 65 feet from the hole, the Italian pro tried his, and miraculously, the ball went in!

Rocca was overcome with emotion, lay on the ground, and cried as he couldn’t believe what just happened. Eventually, he entered the four-hole playoff against Daly, but luck didn’t favor him. The 67-year-old eventually lost the 1995 Open Championship by four strokes, the best he has ever finished at any major in his career. In the end, Rocca did earn the tag for playing one of the best shots in golf’s history, but never a major.

4. Sergio Garcia’s misfortune at the final hole

Near misses have haunted Sergio Garcia’s career far too many times. Seemingly, that’s one of the reasons why he could never win a major more than once. It was the 2007 Open Championship being held at the Carnoustie Golf Links, and Garcia was the clubhouse leader in all three rounds. Going into the final day, he strengthened that lead by four strokes.

At the final hole, Garcia needed a birdie putt to win what could have been his first major, but he missed it and went into a 4-hole playoff against Padraig Harrington. At the first extra hole, the Irish pro carded a birdie while Garcia made a bogey, which cost him the major in the end. He lost the Open Championship by one stroke, and his dream of lifting the Claret Jug eluded him.

3. Tom Watson’s tragic loss against Stewart Cink

Nine months after his hip replacement surgery at age 59, the field was not expecting Tom Watson to take the 54-hole lead and shoot 4 under 206 going into the final round of the 2009 The Open at Turnberry. But he did just that and showed the remarkable form he has always been praised for. While Watson was balancing his bogey and birdie ratio in the final round, Stewart Cink from behind was enjoying a birdie fest.

Yet Watson kept his lead after shooting a birdie on the 17th, as Cink followed him from behind. He had it all in his hands, but the 18th-hole bogey forced the match into a four-hole playoff against Cink. Eventually, the chances of Watson becoming the oldest major winner escaped by six shots, and Cink carded his maiden major win. If things had worked out in Watson’s favor, the American pro would have become a six-time Open winner, a record only held by Harry Vardon.

2. Mark Roe’s disqualification

Mark Roe experienced the most heart-shattering moment of his professional career as he watched the final round of the 2003 The Open as Ben Curtis lifted the Claret Jug, which could have been his. But a mistake cost him the only chance he had to ever win a major. Going into the final round, Roe was just two strokes off the leader.

Roe shot a third-round 67 at the Royal St. George, while his playing partner, Swede Jesper Parnevik, struggled to finish with an 81. The two ended their rounds, added their scores, and, after signing it, went about their day as they gave a few interviews.

Suddenly, Parnevik approached Roe and told him about the costly mistake they had unknowingly made. Unfortunately, Roe signed the Swede’s card and Parnevik signed him, breaking rule 6-6D to face immediate disqualification. After the troubling end, Roe never played the major again and retired three years later, in 2006, without a major win to his name.

1. Tiger Woods breaks down in tears

Just two months before The Open was to be held at Royal Liverpool, Hoylake, the 15-time major champion lost his mentor, father, and everything that Earl Woods was to Tiger Woods to prostate cancer. Throughout the final round, the 48-year-old was a picture of poised manners and did not show any emotions.

As he reached the final hole and drained the final putt, Woods claimed the third Claret Jug of his career. He clenched his fist as the gallery roared and hugged Steve Willimas, crying, which Woods rarely did on the greens. The only wish the 3-time Open winner had was, “I wish he could have seen this one last time.” It was indeed a rare sight and a moment always carved in history, as it was the last time Woods won at the British Open and the first time he won a major without his father, Earl Woods.

Through thick and thin, the Open Championship has witnessed many special moments for the golfers. Moving forward, as the trend goes, it will always be the place for some of the historical moments to take place.