1999 U.S. Open. Payne Stewart and Phil Mickelson. Photo Credit: USGA on YouTube. Payne Stewart speaks to Phil Mickelson after defeating him by one shot in the 1999 U.S. Open. Photo Credit: USGA on YouTube.

The 2024 U.S. Open will be the first held at Pinehurst No. 2 in 10 years. It will also be the fourth U.S. Open at the venue.

Chances are that unless you’re a particularly big fan of Martin Kaymer, the 2014 U.S. Open wasn’t that memorable. Kaymer’s performance was dominant. There was very little drama in what was an eight-shot win. That came nine years after Michael Campbell won his first and only major at the 2005 U.S. Open, grinding out a tough, two-shot victory over Tiger Woods.

In terms of drama, neither the 2005 or 2014 could match what we saw at Pinehurst No. 2 in 1999. But to be fair, regardless of venue, the 1999 U.S. Open has few peers.

And before we shift our attention to the 2024 U.S. Open, let’s look back 25 years at one of the greatest U.S. Opens in history, Pinehurst No. 2’s first U.S. Open, 1999.

Getting to Sunday

Just one year after squandering a big lead in the final round of the 1998 U.S. Open, Payne Stewart quickly put himself in the mix again. He fired an opening round 68 and sat at two-under par, just one shot off of the lead. Stewart backed that up with a one-under 69 on Friday and shared the lead with David Duval and Phil Mickelson heading into the weekend. Saturday was more of a struggle for the field, as Stewart’s two-over 72 was still good enough to give him the outright lead going into the final round.

Stewart being atop the leaderboard was about the only thing that the 1999 U.S. Open after 54 holes had in common with 1998 at the same point. Seven golfers were within four shots of Stewart. Eight golfers were within five shots, the same deficit that Lee Janzen overcame a year earlier to beat Stewart. And it wasn’t just that the leaderboard was tighter after 54 holes.

Mickelson, one of the best players in the world and still looking for his first major, was just one shot behind Stewart. Tiger Woods was just two back of Stewart. World No. 1 David Duval was three shots back, as was 1998 PGA Championship winner Vijay Singh.

This was a tight leaderboard featuring some of the best in the world, all of whom were in — or at least, near — their primes.

As if that wasn’t enough, there was one more subplot. Mickelson was not only looking for his first major win but was also getting ready to be a dad for the first time. His wife, Amy, was pregnant with the couple’s first child. Regardless of where he stood on the leaderboard, Mickelson was clear that was ready to leave Pinehurst at a moment’s notice if Amy went into labor.

Early Sunday drama

John Daly started the tournament well and was only one shot off of the lead after 18 holes. But following  77 on Sunday and an 81 on Saturday, Daly was not in the mix. He did however, create a buzz on Sunday. Daly was not the first or last golfer to express frustration toward the USGA for the setup of a U.S. Open. But the way he did it? That was uniquely Daly.

Daly’s second shot on the eighth hole finished long of the green. Mounded greens are one of Pinehurst No. 2’s most definitive features. Because of that, pros often hit more off the putts from off of the green than they do at most American venues. Daly did that on his third shot, only for the ball to roll back down to his feet. His fourth shot was in the process of doing the same — but Daly didn’t let that happen.

As the ball was rolling back down the hill, Daly whacked it with his putter, sending the ball across the green and into the fairway in front of it.

Hitting the ball counted as his fifth shot and striking a moving ball is a two-stroke penalty. With that, Daly was hitting his eighth shot front in front of the green. He chipped onto the green and three-putted from there for an 11. He shot an 83 for the round and finished +29 over the tournament, the worst score of anyone who made the cut.

“The U.S. Open is not John Daly’s style of golf,” Daly said following his round, H/T ESPN. He was frustrated with where the pins were placed in relation to the slopes. “I’m not going to Pebble Beach next year and watch the USGA ruin that golf course, too.”

Daly didn’t just say that he wouldn’t play the 2000 U.S. Open at Pebble Beach but at any U.S. Open going forward.

“It’s not worth it. This is my last U.S. Open — ever. I’ve had it with the USGA and the way they run their tournaments. The USGA loves to embarrass guys who play in their tournaments.”

Crowning a champion

While the leaderboard heading into Sunday’s round was crowded, the final 18 holes quickly evolved into a four-man race.

Vijay Singh

Singh played a steady final round. He made par on the first seven holes, then made birdies on No. 8 and No. 10 to give himself a great chance coming down the stretch.

When Singh reached the 14th green, he was at even for the tournament and just one stroke off of the lead. It briefly looked as though Singh would take a share of the lead but his birdie putt caught the lip and rolled around — but not into — the hole. Singh was still in contention but after making bogey on No. 16 to fall to one-over, it was clear that he’d need to birdie at least one of the final two holes to have a chance.

It didn’t happen. Singh made par on both No. 17 and No. 18.

His final round was not bad by any means. He only made one bogey, something that any golfer in contention would gladly take in the final round of any U.S. Open. But starting the day three shots back, Singh needed to make some earlier birdies. Failing to do so left him little margin for error coming down the stretch. He finished the tournament one-over.

Tiger Woods

If Singh was too steady to start his final round, Woods was too erratic. He made two birdies and two bogies over the opening five holes. After making par on five straight holes, Woods made a bogey on No. 11, moving Tiger to two-over and seemingly taking him out of the mix.

But it’s hard to ever count Tiger Woods out of a tournament.

He made birdie on No. 14 and No. 16 to move within a shot of the lead. The birdie on No. 16 was notable since it was such a challenging hole through the tournament and particularly on Sunday. It also created a loud roar, something Stewart and Mickelson heard on the 16th tee just one group behind Tiger.

Despite that, Woods still had work to do. And he made life difficult for himself on the next hole by hitting his tee shot into a greenside bunker on the par-three 17th hole. Tiger’s bunker shot was fine, leaving him a makeable par putt. But he hit the ball too hard and it lipped out for a bogey. To have any chance at winning, Woods needed some help from Stewart and/or Mickelson. But first, he needed a birdie on No. 18.

He got off to a good start, lacing a long drive down the fairway to leaving himself a wedge into the green. The wedge, while not perfect, left Woods with a chance. His putt was beautifully struck and and nearly dropped. It’s hard to imagine that he could have rolled the ball any better. Despite that, it didn’t drop. With that, Tiger finished one-over, tied with Singh.

Payne Stewart and Phil Mickelson

More major triumphs awaited both Woods and Singh in the near future. But with both finishing at one-over, it was clear that the champion would come from the final pairing. Would it be Stewart or Mickelson?

You probably know the answer to that question. But you may not remember what led to it.

First, imagine a scenario where a pair of golfers play 18 holes together and both finish the day at even-par for the day. Golfer A makes four bogeys and four birdies. Golfer B makes 16 pars, one birdie and one bogey. Now, one of those golfers is Phil Mickelson, which one is it?

If you thought Mickelson was Golfer A, you’re in what we’re guessing is the majority group — but you’re wrong. Mickelson was largely steady throughout the round. Stewart, meanwhile, was all over the place, going birdie-bogey-birdie on the first three holes. Things stabilized somewhat from there, as Stewart made par on every remaining hole on the front nine. Mickelson made a birdie on seven to narrow the gap back to one shot.

A Stewart bogey on No. 10 drew the two to a tie. Mickelson then took a one-shot lead when Stewart bogeyed No. 12. While Stewart regained a share of the lead with a birdie on No. 13, that was brief. A bogey from Stewart on No. 15 gave Mickelson a one-shot lead with three holes to play. The tournament was decided on those three holes — specifically those three greens.

While Stewart and Mickelson both hit great drives on the challenging 16th hole, both missed the green with their second shots. Mickelson’s chip shot was not particularly good, especially for his standards. Still, it was far better than Stewart’s which took par out of the question and made making even a bogey seem like a challenge — or so it seemed. Stewart drained his long putt to save par. Mickelson pulled his much shorter putt hard left, making bogey. With that, it was a two-hole tournament.

It looked like both men would birdie the 17th hole, as both hit their tee shots close. Again, it came down to a putting contest and again, Stewart won. Mickelson, as he’d done on No. 16, pulled his putt. Stewart, meanwhile, calmly rolled his in. Mickelson could have been up by one, two or even three shots going to No. 18. Instead, he walked to that tee box exactly as he did when went to the first tee hours earlier, trailing Stewart by a shot.

Stewart created a potential opening when his tee shot landed in the thick rough of the par-four finishing hole. With no realistic chance to make the green in two, Stewart opted to lay up. He hit the ball back into the fairway, well short of the green. Mickelson’s tee shot found the fairway and his second shot found the green. He still had a chance to make birdie, but it was going to require a big putt.

Stewart’s pitch was good. He didn’t leave himself a gimmie by any means. But he got the ball onto the right level and left himself a straight, uphill putt for par. But would that putt be for a spot in a playoff or an outright win?

Mickelson’s putt was well struck but he played too much break. He tapped his final putt in to finish the hole, round and tournament at even-par. Looking ahead seven years, playing the final hole this way would have suited Mickelson well. Here, he had to wait.

Which brings us to the end of the tournament, the part you’ve probably seen before and will certainly see again on replay. Stewart made clutch one-putts on No. 16 and No. 17 and saw no reason to deviate on No. 18.

He rolled his putt perfectly into the hole. In a moment that is now a statue at Pinehurst No. 2, Stewart, with his right foot off the ground behind him, put his right fist into the air in celebration.

It was Stewart’s third major, second U.S. Open and unfortunately, the final win of his storied career.

After an embrace with his caddie, Stewart walked over to Mickelson, put his hands on Mickelson’s cheeks and said, “Good luck with the baby. There’s nothing like being a father.”

It was poignant moment at the time that became more poignant in the coming months.


Stewart’s U.S. Open win came on June 20, 1999. Four months later, on Oct. 25, 1999, he was gone.

He was one of six people killed in a plane crash. The cabin did not pressurize, which incapacitated everyone on board, including both pilots, shortly after takeoff. While the flight was supposed to be from Orlando to Dallas, the plane ended up getting all the way to South Dakota before running out of fuel and crashing.

Stewart was 42.

In happier news, Mickelson became a father for the first time one day after the U.S. Open ended. He’d have to wait a little longer to shed the “Best player to never win a major” label. That came in 2004, when Mickelson won the Masters.

While Mickelson now has six major championships, he’s yet to win his national championship. He’s finished second (or tied for second) six times. Other than 1999, the most notable second-place finish was in 2006, when Mickelson doubled-bogeyed the final hole, needing a par to win outright and a bogey to get into a playoff. With three Masters titles, two PGA Championships and one British Open, the U.S. Open is the only major keeping Mickelson from the career Grand Slam.

Things went well for both Woods and Singh following their near misses. Tiger won his second career major at the PGA Championship in 1999. Singh won his second major at the Masters in 2000, the only major not won by Tiger that year. Woods’ victories at the three other majors in 2000 along with the 2001 Masters made him the reigning champion at all four majors simultaneously. Or, in simpler terms, he won the Tiger Slam.

Woods and Duval would trade the World No. 1 ranking through the summer of 1999. Tiger regained the top spot in the middle of August and held until September of 2004, when Singh claimed it. That was shortly after Singh won his third career major at the 2004 PGA Championship. Woods and Singh exchanged the top spot in 2005 but when Woods regained it June, he didn’t lose it again until 2010.

Of course, we can’t leave without talking about Daly. Despite his frustration in 1999, Daly returned to the U.S. Open in 2000, though that didn’t go any better. Daly finished the opening round with a 14 on the par-five 18th hole to shoot an 83. He withdrew immediately after. Daly returned to the U.S. Open twice more, once in 2002 and again in 2005. Coincidentally, the 2005 U.S. Open was also played at Pinehurst No. 2.

Knowing what we know now, it’s impossible to watch any of the 1999 U.S. Open and not be overcome with bittersweet feelings. In victory, Stewart held off the greatest player of the era (and arguably of all-time) along with two of his most formidable rivals.

And in the immediate aftermath of that victory, he reminded the man he just defeated of far greater moments ahead.

For a lot of golf fans, the final memories of Stewart either came at Pinehurst or at the Ryder Cup that September. Colin Montgomerie, Stewart’s opponent on Sunday, had been subjected to heckling throughout the day. While the American victory was secure following a dramatic comeback, Stewart and Montgomerie were still on the course. On the 18th green, in an act of sportsmanship, Stewart picked up Montgomerie’s ball marker, conceding Montgomerie’s putt and with it, the match with Stewart.

Stewart was an original. All you had to do to know that was to see how he dressed on the course. He was a fierce competitor on the course but also a man with priorities. Both features were on display in the final round at Pinehurst 25 years ago.

He was taken far too soon. But for many golf fans, the final memories of Stewart are, much like the 1999 U.S. Open, just about perfect.

[ESPN.com, Photo Credit: USGA on YouTube]

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