Sept. 21-26, 2021 Whistling Straits, Kohler, WI

“I have a good feeling about this.”

That one line, offered up by U.S. captain Ben Crenshaw on the eve of the final day of the 1999 Ryder Cup, would become lore after the final chapter was written at The Country Club. An unprecedented comeback capped an emotional week for both sides, as the Americans stormed back from a sizeable deficit to beat the Europeans in one of the most dramatic editions of the biennial matches.

Let’s take a look back on the key players and turning points from an epic showdown in New England – one that is now remembered for far more than the standout shirts worn by U.S. players on the final day:

The Scene

The Europeans had won the previous two Ryder Cups, including an emphatic victory on home soil at Valderrama in 1997, and were looking to make it three in a row for the first time in the history of the event. Taking the captaincy reins from Seve Ballesteros was England’s Mark James, a soft-spoken veteran on the other side of the emotional spectrum from the fiery Spaniard. The Americans were led by Crenshaw, a two-time Masters champ who had made four teams as a player.

The Stars

The matches included all four major champions from 1999: Payne Stewart (U.S. Open) and Tiger Woods (PGA Championship) played for the Americans, while Jose Maria Olazabal (Masters) and Paul Lawrie (The Open) teed it up for Europe. Woods was on the cusp of his Tiger Slam and nearing the peak of his considerable talents. Alongside world No. 2 David Duval, the two headlined an American squad that featured nine of the top 14 players in the world. By comparison, the Euros had only Colin Montgomerie (No. 3) and Jesper Parnevik (No. 15) among the top 20. Their roster featured a whopping seven rookies, including future stalwarts like Sergio Garcia and Padraig Harrington, along with Lawrie and the man who lost a late lead to him at Carnoustie, Jean Van de Velde.

The Turning Point

Crenshaw’s Saturday night speech came with the U.S. trailing 10-6, knowing full well that no team had ever erased a deficit of more than two points in Sunday’s singles. But the tide may have turned with a pair of decisions made by the opposing captain: first, James’ choice to shelter rookies Van de Velde, Andrew Coltart and Jarmo Sandelin. None played in any of the four sessions across the first two days, and all ultimately lost their singles’ matches. The other miscue (in hindsight) was putting his best players toward the back of the Sunday lineup despite holding a sizeable lead. That decision allowed the Americans to build some early momentum and get a boisterous home crowd cheering one birdie after another, leading to a comeback for the ages.

The Result

The Americans flipped the script with incredible speed, winning each of the first seven points of the day to turn a 10-6 deficit into a 13-10 lead. Included in that run were emphatic wins by Woods, Duval and Phil Mickelson, while Davis Love III beat Van de Velde, 6 & 5. Harrington and Lawrie eventually put some blue on the board, but the Americans were leading 14-12 and on the cusp of a monumental win when Justin Leonard surveyed a lengthy birdie putt on the 17th hole while tied with Olazabal. The putt improbably found the bottom of the cup, sparking a raucous celebration that spilled across the putting surface. When Olazabal failed to match with a birdie of his own, the Americans were assured of a decisive half-point and ultimately won by a 14 ½ to 13 ½ margin.

The Legacy

The final point went to Europe, when Stewart conceded the 18th hole to Montgomerie with the overall outcome already decided. The magnanimous gesture proved to be one of his last on the course, as he died in a plane crash one month later.

It was the final Ryder Cup appearance for Mark O’Meara, as well as teammates Tom Lehman, Jeff Maggert and Steve Pate. Brookline served as a launching pad for Garcia, who went 3-1-1 as a rookie while creating a formidable duo with Parnevik. Van de Velde, Coltart and Sandelin never played another Ryder Cup match.

The outcome was a bitter defeat for the Europeans but did little to slow their Ryder Cup momentum: they went on to earn the elusive three-peat from 2002-06, then returned the favor on the Americans in 2012 by erasing a 10-6 deficit on the final day at Medinah. More than two decades after Crenshaw’s prescient presser, the Americans have only won two subsequent Ryder Cups.

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