The Ryder Cup will celebrate its centenary in 2027 and over the years there has been no shortage of drama and unforgettable moments. There has been controversy, animosity and of course lots of sensational golf, and there have also been some incredible comebacks.
Since the contest became a match between USA and Europe, in 1979, it has been relatively even. Europe have had the edge, winning 13 of 23 matches as of 2026, with USA triumphing nine times and one tie. But while the overall stats are balanced, we have seen periods of dominance, especially by Europe, as well as big wins for both sides, and also some real rollercoaster matches that have swung to and fro.
One of the greatest comebacks in Ryder Cup history came in 1999. The so-called Battle of Brookline took place in Massachusetts, at Brookline’s The Country Club venue. It was the 33rd edition of this iconic golfing battle, and with Europe having won the previous two tournaments, including in New York in 1995, the hosts were desperate to avoid a hat-trick of losses.
USA Start as Strong Favourites
As is often the case at the Ryder Cup, the USA started the 1999 contest as big favourites. These days Europe are often fancied on home soil, but it was different back then. Europe had been 15/8 in 1995 and a massive 2/1 at home in 1997, thanks to fielding five rookies and the emergence of a certain Tiger Woods. Ahead of the contest in the suburbs of Boston, the hosts were as short as 2/7 and it was easy to see why.
They were desperate for revenge, had home advantage and, as usual, had by far the better team – on paper. Europe had seven rookies plus three players with just one Ryder Cup appearance. They had the world numbers three and five, in Colin Montgomerie and Lee Westwood respectively. But they also had six players ranked outside the sport’s top 44, including four outside the top 65.
In contrast, the home team’s only rookie was world number two David Duval. They boasted a dominant world number one in Tiger Woods, plus eight other players inside the top 16. Their lowest-ranked golfer was Steve Pate, the world number 28. The bookies and most punters saw only one winner, and who could disagree with such an assessment?
Europe Make Dream Start
On the opening Friday Montgomerie partnered fellow Scot Paul Lawrie in a foursomes match against Phil Mickelson and Duval. The Scots were superb and won 3 & 2 and when Woods’ poor competition record continued in match two, as he and Tom Lehman lost 2 & 1, the away side may have dared to dream of an upset.
At the end of the morning’s play, they were 2.5 – 1.5 up but at the end of the day, when Westwood and Darren Clarke beat the US fantasy pairing of Woods and Duval, the top two in the world, that lead had extended to 6 – 2. The European duo clinched the match on the final hole too, which made it feel all the more important.
Spoils Shared on Saturday But USA Left with Mountain to Climb
Europe won two of the four morning matches 3 & 2 but the hosts stuck in there, winning both others on the final hole. That meant Europe maintained their four-point cushion into the afternoon, and when that session too ended 2-2, thanks to two halved matches and one win apiece, the visitors knew they would take a huge 10-6 lead into the singles.
They were helped a great deal by Jesper Parnevik and Sergio Garcia pinching a half on the 18th against Duval and Davis Love III. Love missed a birdie putt on 18 to win the match and from a similar length Garcia holed to nick half a point and maintain his and his partner’s unbeaten record. It gave Europe a big boost and they were heavily fancied to win the Ryder Cup for the third time in a row and second time running on foreign soil.
History Against Hosts
Prior to this clash, no team had ever come back from more than two points behind and won on the last day. With a lead of four points, European skipper Mark James, who had played in the Ryder Cup seven times, including the success in 1995, had plenty of room to manoeuvre from a historical perspective.
The flip side of that is that his counterpart, Ben Crenshaw, himself a veteran of four Ryder Cups, had nothing to lose. Gentle Ben, who won the US Masters in 1984 and 1995, would not have been one for screaming, shouting and chest-thumping. He simply reminded his players that hardly anyone expected them to win, so there was no pressure. At the same time, he told them that he believed that not only would they win, but they could whitewash Europe, such was his faith in them all.
In the Saturday night press conference, he ended things by saying “I’m going to leave y’all with one thought: I’m a big believer in fate and I have a good feeling about this match. That’s all I’m going to tell you.” After the victory was (spoiler alert!) sealed, he revealed that he had told Team USA they were capable of winning every match because “that’s how strongly I believed.”
USA Win in Style But Without Class
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With the benefit of hindsight it is easy to suggest that James got his playing order wrong. He saved most of his big guns for the end, while Crenshaw front-loaded his lineup, knowing that the only chance his team had was to put early red on the board and gain momentum.
Hindsight might also suggest that James erred by not including three of his rookies before the singles. These two factors combined to mean that three of Europe’s weakest golfers, rookies Andrew Coltart, Jarmo Sandelin and Jean van de Velde, got their first taste of Ryder Cup action against Tiger Woods, Phil Mickelson and Davis Love III, in matches five, three and four respectively.
Davis Love got the first American point, winning 6 & 5, before Tom Lehman took the scalp of Westwood in the opening match to make it 10-8. Game on. The dominoes fell, with Mickelson crushing Sandelin 5 & 3 to make it 10-9 and Hal Sutton beating Darren Clarke to make it 10-10. Duval and Woods won and all of a sudden it was 12-10 to the hosts, with Europe’s highest- and lowest-ranked players all losing.
The US won the first six matches, and although Europe “won” the second half of the draw 3.5 to 2.5, it was too little, too late. USA won by 14.5 to 13.5, making history with one of golf, and sport’s, greatest comebacks.
It was a stylish comeback but sadly they proved unable to win with class. Jose Maria Olazabal had been four up against Justin Leonard with seven holes to play. He lost three holes in a row and then Leonard sank a 40-footer to draw level. At the next, the 17th, he then sank another monster putt for a birdie. That all-but sealed victory and the US team, wives and TV camera crew stormed the green, even treading on Olazabal’s line.
The key phrase, though, was “all-but”: Leonard’s opponent had a significantly shorter putt to tie the hole and keep the match, and the Ryder Cup, alive. The American celebrations were premature, inappropriate and unfair. Olazabal missed, obviously not helped by the long delay to clear the green, and the US had done the impossible, completing the greatest comeback in Ryder Cup history to that point.
Sadly the feat was somewhat tainted by that affair and various other incidents, not just on the frenzied final day. Montgomerie suffered terrible abuse, skipper James said that his wife had been spat at, while Sam Torrance labelled Lehman’s behaviour as disgusting and there were even allegations of a marshal cheating in the USA’s favour. Even so, some comeback!