Colin Montgomerie holed a two-foot par putt worth US$340,000 (£240,000) on the third play-off hole to beat defending champion Fred Couples in the Skins Game at Landmark Golf Club, California.
The foursome halved the 16th and 17th holes worth $70,000 each and went to a play-off after halving the $200,000 18th hole. Fiji's Vijay Singh and Spain's Sergio Garcia were eliminated on the first extra hole, the par-four 14th, after missing their birdie attempts while Montgomerie and Couples made theirs.
Montgomerie and Couples both parred the 183-yards 15th, the second play-off hole, and went to the 563-yard 18th.
Couples was in trouble from the start on the hole, driving into the bunker, hitting his second shot onto a golf cart into a bush and then saw his third shot reach the water.
Montgomerie found the green with his third shot and his 20-foot birdie attempt stopped two feet from the cup leaving him with a tap in for the victory.
The amount won by Montgomerie on 18 was the second-largest total on one hole in Skins Game history.
Competing in his first Skins Game, Montgomerie became the sixth player to win in his initial appearance. He finished with six skins and just under £300,000, a Skins Game record for a newcomer.
Singh collected four skins and £185,000 in his first Skins Game. Garcia, who led after Saturday's front nine with four skins, ended up with five and £140,000. Couples, who earned a record £450,000 last year, had three skins and £90,000.