Sept. 25-Oct. 1, 2023 Marco Simone Golf & Country Club, Rome, Italy

The U.S. has 27 victories in the Ryder Cup (27-14-2 all-time), but none was more memorable than its 1999 triumph at The Country Club in Brookline, Mass. After two frustrating days of team play, the U.S. entered Sunday’s singles session trailing 10-6. To that point in the history of the event, no team ever had come back from more than two points down in singles. But the U.S., under the guidance of Texan Ben Crenshaw, went out and won the first six matches on Sunday, then added two and a half more points to wrestle the cup from Europe, 14.5-13.5. (Had the teams tied 14-all that day, Europe would have retained the cup.) 

Here are 15 interesting nuggets you may not know or might have forgotten about the 1999 Ryder Cup: 

• Tom Lehman hit all 16 greens in regulation in defeating Lee Westwood, 3 and 2, in Sunday’s opening singles match. (He said he hit it as well as he had in his 1995 singles victory over Seve Ballesteros, but this time made more putts.) But Lehman didn’t deliver the first U.S. point that Sunday. Davis Love III did with a 6-and-5 throttling of Jean van de Velde. 

• The 10-6 deficit for the U.S. through two days was shocking for several reasons, but mostly this: The U.S. had 10 players on its team ranked 16th or better in the world, including three of the top four (No. 1 Woods, No. 2 David Duval, No. 4 Love). Europe had only three players in the top 16: Colin Montgomerie (3), Lee Westwood (5) and Jesper Parnevik (15).

1999 ryder cup

• Justin Leonard is remembered as the hero in that Ryder Cup for bouncing back from a 4-down deficit (after 10 holes) against José María Olazábal and sinking the clutch 45-footer for birdie at The Country Club’s 17th hole that would secure the half-point the U.S. needed for victory. But do you know he left Brookline still not having won a full point? Olazabal birdied the last hole to halve him, leaving Leonard at 0-3-5 in his first two Ryder Cups (1997, 1999). He wouldn’t secure his first full point until nine years later, at Valhalla, when he and fellow Texan Hunter Mahan won their opening foursomes match against Henrik Stenson and Paul Casey. 

• On a hunch, Crenshaw played Leonard over Jeff Maggert on Saturday afternoon, and Leonard didn’t play well, prompting NBC’s Johnny Miller to say on air that Leonard probably shouldn’t have been out there. It fired up Leonard and the U.S. team when a few players read the comments the next morning before singles. But here was Johnny on Leonard’s heroic putt on the 17th green: “It had to be the greatest putt in Ryder Cup history, there’s no doubt about it.” 

WATCH: Highlights from Furyk/Garcia '99 singles match

• Parnevik and Sergio Garcia played four team matches under European captain Mark James and went 3-0-1. In their first match on Day 1, Parnevik-Garcia took down Tiger Woods and Tom Lehman in foursomes, 2 and 1. Europe captain Mark James had seven rookies on that 1999 team, and you probably remember that three (Jarmo Sandelin, van de Velde, Andrew Coltart) did not appear until the Sunday singles. (Crenshaw later told Golf Digest, “I just could not believe he sent them out three in a row.”) The rookies played in the 3-5 slots and didn’t get very lucky in the opponents they drew. Sandelin lost to Phil Mickelson, 4 and 2; Van de Velde lost to Love, 6 and 5; and Coltart lost to Woods, 3 and 2. 

• Mickelson and Sandelin knew they’d be in for a tense singles match, as they had some history and weren’t the best of friends. On the second hole of their match, Sandelin hit a shot to 3 feet. Mickelson wasn’t about to give it to him, and was waiting for Sandelin to mark his ball so that he could play his next shot. Sandelin fumbled around in his pockets for a marker, but didn’t have one. “Jarmo, do you need a coin?” yelled a fan from across the gallery ropes. He nodded that he did. A cascade of coins from the crowd then descended upon him. As Jim “Bones” McKay, caddie for Mickelson at the time, told The Boston Globe, “I’m telling you, it was raining coins." Mickelson two-putted for his par and Sandelin missed his putt. 

• The U.S. players ranked in the world top 10 that week: 1. Woods; 2. Duval; 4. Love III; 8. Payne Stewart; 10. Hal Sutton.

• Remember those, ahem, busy burgundy shirts that the U.S. team wore on Sunday, showing great U.S. snapshots from Ryder Cups past? One of those shirts (new, not used) actually sold for $3,906 at auction just this week. The 1999 Ryder Cup lives on.

MORE: A brief history of the '99 U.S. Ryder Cup shirt

• In his singles match against Woods, Coltart hung tough for a player participating in his very first Ryder Cup match. On the fourth hole, he stuffed a shot to 3 feet; Woods needed to answer and he did, hitting his approach to 3 feet. As they walked to the green, Coltart said to Woods, “Let’s go to the next.” And Woods said, “No, let’s putt these.” After his 3-and-2 victory, Woods would add, “For some reason, that got me all fired up.”

1999 ryder cup

• Padraig Harrington was one of Europe’s seven rookies that year, and many U.S. fans were getting their first glimpse of the future three-time major champion. But Harrington was painfully slow. On a couple of his holes on Sunday, he would walk all the way to the green from more than 100 yards out to check out the putting surface, and his slow play was wearing on Mark O’Meara, his opponent. Said NBC’s Dick Enberg, who was on the call with Johnny Miller, “Harrington’s pre-shot routine gives new meaning to the Boston Marathon.” 

• Trailing 10-6 on Saturday evening, U.S. captain Ben Crenshaw wagged his finger and told the media, "I have a feeling about this," and that night, George W. Bush, then governor of Texas, addressed the players, wives and caddies in the team room and told them the story of commander William Barret Travis and his refusal to surrender at The Alamo in 1836. Crenshaw is an astute student of the game and its history, and it wasn't lost on him that Leonard's clinching putt had taken place on the green at No. 17, just across the street from where 1913 U.S. Open champion Francis Ouimet had once lived. (Once José María Olazábal missed a putt to tie Leonard at 17, going 1 down, Crenshaw knelt and kissed the green three times.) In the celebration afterward, Crenshaw said, "The Country Club has been very kind to Americans in its storied past, and it proved it today." 

• Europe had two captain’s selections that year, and used them on Coltart and Parnevik. One interesting player left off the team that year was Bernhard Langer. In a stretch of 11 Ryder Cups (1981-2002) that was the lone one in which Langer did not participate. He played 42 matches, had an all-time record of 21-15-6, and in 2004, he captained Europe to a lopsided victory over the U.S. Longer was 42 in '99; in fairness to captain Mark James, though Coltart only played once (and lost), Parnevik finished 3-1-1. 

• Montgomerie needed two putts at the last hole to defeat Payne Stewart in singles. Stewart, realizing how much heat Montgomerie had withstood from a partisan crowd that afternoon, never made him putt, conceding the hole in a classy gesture. In eight singles matches in the Ryder Cup, Montgomerie never was beaten. His record: 6-0-2. 

• A memorable scene: Spain’s José María Olazábal, who’d struggled with his ball-striking that week, standing on the second-floor balcony outside Europe’s team room Sunday evening, tossing some of the drivers that were in his locker out into the crowd. 

• The 1999 Ryder Cup marked Payne Stewart’s final appearance in the event, as on Oct. 25 of that year, he was one of six people killed when the Learjet in which he was flying (destination: Dallas), crashed in South Dakota. Stewart was 42, and after the night of that 1999 victory, he and Hal Sutton had a conversation about one day being Ryder Cup captains. Sutton was captain in 2004; Stewart never got his chance. 

1999 ryder cup

Stewart had arrived to Brookline a little rusty, having spent lots of time in the preceding weeks with his wife, Tracey, and their two children. He went 0-2-1 that week, but relished the team victory, telling his wife that it had been the perfect finish to a great season (he’d won the U.S. Open at Pinehurst No. 2 in June). From the U.S. team afterparty that night, there is a picture of Stewart wearing American flag sweatpants and a t-shirt, with a cigar in his mouth, holding champagne in one hand and a beer in the other. He is dancing upon a piano. Phil Mickelson, the man Stewart had edged for that U.S. Open crown, has the picture on a wall in his house. It’s the last time he ever saw Payne Stewart.

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