Remembering The 1999 Brookline Ryder Cup

The Country Club, affectionately known as Brookline, has hosted the US Open on several occasions, and does so again in 2022. However, it was also the scene of one of the greatest – and most controversial – Ryder Cups of all time.

Heading into the final day, the Europeans held a commanding 10-6 lead, leaving Mark James’ team needing just four more points to retain the cup. That reckoned without a day that had just about everything, though.

The night before, US captain Ben Crenshaw had wagged his finger while telling the media: "I have a feeling about this," and on that infamous Sunday, it didn't take long for the pendulum to swing back their way as the US team won the first six matches to give them a 12-10 lead. 

Padraig Harrington then helped settle Europe’s nerves with the team’s first point of the day, over Mark O’Meara, but it wasn’t enough to spark a comeback. Further US wins, for Steve Pate over Miguel Angel Jiminez and Jim Furyk over Sergio Garcia, ensured the hosts kept the upper hand despite Europe’s Paul Lawrie beating Jeff Maggert.

All this left the US 14-12 ahead with just two matches to finish, meaning Crenshaw’s team needed just half a point to win in front of a notably raucous and partisan crowd. Europe, meanwhile, needed to win both to tie and retain the cup. Then things got really interesting.

For most of the time in those final two matches, it had looked like the drama would come between Colin Montgomerie and Payne Stewart, with the pair trading the lead on several occasions. Montgomerie would eventually claim victory, but the decisive moments came in the match between Jose Maria Olazabal and Justin Leonard.

With just seven holes to play, the Spaniard was cruising at 4 up, but that advantage vanished over the next four holes, including a 40-foot putt from Leonard at the 15th. That wouldn’t be the last monster putt of his round, though. Two holes later, he holed another 40-foot putt for birdie, leaving Olazabal needing to hole his 25-foot putt to stay in the contest. Before he could attempt it, though, the US team, their wives and the NBC camera crew ran onto the green celebrating prematurely, with the cameramen seemingly stepping in Olazabal’s line. 

Those celebrations marked the moment events finally spilled over after what had been a hostile experience throughout for the Europeans, including suffering abuse from the crowd. Meanwhile, even the US players were caught up in over-the-top behaviour, with Europe's vice-captain, Sam Torrance, later saying: "It was the most disgraceful and disgusting day in the history of professional golf. The spectators behaved like animals and some of the American players, most notably Tom Lehman, acted like madmen."

When Olazabal finally got the chance to take his shot, he failed to sink it, leaving Leonard one up with one to play – an unassailable lead. Olazabal holed a birdie on the 18th that halved the match. Still, the damage was done, and one of the most thrilling and controversial comebacks in Ryder Cup history was complete, with the US winning 14.5 to 13.5.