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How Tiger Woods nearly blew a five-shot lead to a teenage Sergio Garcia on Sunday at the 1999 PGA Championship

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The 1999 PGA Championship may have been the final major of the millennium, but it looked set to usher in a new era in the golfing landscape as the two youngest players in the field battled it out for the title at Medinah.

It is difficult to imagine now, but Tiger Woods went into the 1999 PGA Championship having not won a major in more than two years, since the 1997 Masters. Woods had however, finished in the top 10 in five of his previous seven major appearances.

Sergio Garcia meanwhile, was much more of an unknown quantity in the majors. The Spaniard was the low amateur at Augusta National that year, finishing 38th. But he had missed the cut at The Open Championship, his first major as a professional.

Garcia would more than make up for that in Illinois in August.

How Tiger Woods held off Sergio Garcia to win the 1999 PGA Championship

Heading into Sunday at Medinah, Woods was tied for the lead with Mike Weir at 11 under par. Garcia was two shots back, tied for third with Stewart Cink. Garcia had actually been leading by two after the first round.

However, as Woods walked off the 11th green on the last day, it appeared that he had more than one hand on the Wanamaker Trophy. He led by five, and it seemed that he was closing in on another emphatic major championship victory.

Three dropped shots in the next two holes for Woods opened the door for Garcia. And the 19-year-old – who was playing in the group in front – threatened to capitalise with a birdie of his own on the 13th hole. Garcia sent out a message by staring back at the tee where Woods was waiting after finding the bottom of the cup.

Sergio Garcia hits a recovery shot on the 16th hole at Medinah during the 1999 PGA Championship
Photo by ROBERTO SCHMIDT/AFP via Getty Images

But if there is one iconic shot from the 1999 PGA Championship is known for, it is undoubtedly the one which helped Garcia save par on the 16th hole and saw the starlet dance into the hearts of many golf fans.

Garcia’s tee shot had left him up against a tree and it seemed inevitable that he would have to chip out and take his chances that he could get up and down from distance and keep the pressure on Woods.

Garcia however, was prepared to risk it all and swung as hard as he could with a six iron. He showed at least some concern for his own safety by turning his head away at impact.

But the greats know when the contact is exactly right. And Garcia almost immediately started to run after the ball; as if he was in a race to reach the putting surface first. Somehow, his audacious approach had left him with the longest of birdie putts.

It was not enough in the end. Both men made par on their final two holes to ensure that Woods held on.

The greatest chapter in what threatened to be an amazing rivalry between Tiger Woods and Sergio Garcia

Incredibly, Woods would not win another major by one shot again until The Masters in 2019. And his comments after the final round highlighted just how far Garcia pushed him.

“To come out of it on top took everything out of me,” he said, as reported by ESPN. “I just tried to hold him off and did the best I could.”

It did seem that Garcia had still put the golfing world on notice. He would make his Ryder Cup debut the following month and won 3.5 points at Brookline – no player on either side won more. And it appeared to be a matter of time until his maiden major victory was secured.

Few would have ever imagined that it would be more than 17 years before that major arrived, with Garcia winning The Masters in a playoff with Justin Rose in 2017.

Woods and Garcia would cross paths on a number of occasions in the years that followed the 1999 PGA Championship. But the duels which followed never quite hit the same heights as that remarkable final day at Medinah 26 years ago.