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Justin Leonard’s putt on the 17th hole at Brookline is either one of the most famous or infamous putts in Ryder Cup history, depending on your rooting allegiance. Leonard sank a 45-foot birdie putt. When Jose Maria Olazabal missed his birdie bid, Leonard went 1 up, assuring the U.S. of at least a half-point (the match did end in a halve) and clinching the cup. The Americans’ rally from a four-point deficit entering the singles was the largest rally in Ryder Cup history. From the European side, the lasting memory is a sour one, of U.S. players (and wives) storming the green to congratulate Leonard before Olazabal had a chance to putt.
2 / 20
Jack Nicklaus has always said that the Ryder Cup should be more about camaraderie and less about competition. In 1969, Nicklaus put his metaphorical money where his mouth was. Nicklaus had just made a 5-foot putt on the 18th hole, and Jacklin needed to make his 2-footer to halve the match and give the Ryder Cup its first tie. But Jacklin never got to make the stroke. Nicklaus – much to the surprise and consternation of his teammates and U.S. captain Sam Snead – had picked up the Englishman’s coin.
3 / 20
Tiger Woods and Phil Mickelson. A dream team, right? Why wouldn’t you pair them? What could possibly go wrong? But as it turned out, the dream turned into a nightmare. Woods and Mickelson were supposed to set the tome right from the beginning by going out first in the Friday morning fourballs, but they lost, 2 and 1, to Colin Montgomerie and Padraig Harrington. It was more of the same in the afternoon foursomes, as they fell to Darren Clarke and Lee Westwood. U.S. captain Hal Sutton tried to cut his losses by dissolving the pairing, but the damage had been done and the U.S. was thrashed, 18 ½ to 9 ½.
4 / 20
The “Battle of Brookline” Ryder Cup had already been decided, but Payne Stewart and Colin Montgomerie were the last match still on the course. On the 18th green, Stewart conceded the match to Montgomerie, who had been unmercifully heckled by American fans. ''Colin didn't deserve to have to stand over this putt and try to make it,'' Stewart said. ''We had already won the Ryder Cup; that's what it is, a team event. My individual statistics don't mean anything in the Ryder Cup, and I wasn't going to put him through that.''
5 / 20
The U.S. won at Kiawah Island, but Mark Calcavecchia was an emotional casualty of the “War by the Shore.” Going out third in singles, Calcavecchia went 5 up on Colin Montgomerie, and held a 4-up lead with four holes to play. Then the wheels came off. Calcavecchia lost the final four holes, including losing to Monty’s 5 at the par-3 17th when Calcavecchia’s tee shot didn’t get halfway to the green before splashing down. A distraught Calcavecchia retreated to the beach afterward before being coaxed back for the victory celebration.
6 / 20
The “War by the Shore” Ryder Cup came down to a 6-foot par putt by Bernhard Langer. Had he made it, he would have beaten Hale Irwin and given the Europeans a 14-14 tie. Because the Europeans were defending champions, that would have allowed them to retain the Cup. But the putt slid just past the right edge of the cup, and the U.S. had a 14 ½-to-13 ½ win.
7 / 20
Two of the feistiest figures in golf first clashed in their 1989 Ryder Cup singles match, when Azinger refused to agree to Ballesteros taking a ball out of play because of its condition. But the rivalry really amped up in 1991, when Azinger and Chip Beck took on Ballesteros and Jose Maria Olazabal in the Friday foursomes. The Europeans called out the Americans for violating the one-ball rule. The bad blood included Ballesteros referring to the U.S. team as “11 nice guys and Paul Azinger” and Azinger calling Ballesteros the “king of gamesmanship.” The two eventually buried the hatchet, and when Ballesteros died in 2011, Azinger said “Seve was the most passionate player I have ever faced.”
8 / 20
There wasn’t much drama in the 2006 Ryder Cup in Dublin as the Europeans ran away with an 18 ½-to-9 ½ victory. But the competition has seen few more emotional moments than the ovation that greeted Darren Clarke’s appearance on the first tee on the opening day. Clarke was just months removed from having lost his wife, Heather, to cancer. He went on to win all three of his matches, including his singles duel with Zach Johnson. Clarke said it was his wife’s dying wish that he play in the Ryder Cup.
9 / 20
The biggest deficit overcome going into singles in Ryder Cup history is four points, first done by the Americans in 1999 at Brookline. Europe matched the feat in 2012, thanks largely to Ian Poulter. The Englishman won all five of his matches, teaming with Justin Rose to beat Bubba Watson and Webb Simpson in foursomes, teaming with Rory McIlroy to beat Jason Dufner and Zach Johnson in fourballs, then winning his singles match against Simpson.
10 / 20
Europe went into the final day tied with the United States, 8-8. Hoping to gain an early advantage, Europe captain Tony Jacklin front-loaded his lineup, sending Seve Ballesteros out first against Fuzzy Zoeller. Three up at the turn, Ballesteros saw his lead dwindle until, on the final hole, he needed a par to halve the match. From 245 yards in a fairway bunker, Ballesteros carried the water hazard and knocked the ball on the green, setting up his par. U.S. captain Jack Nicklaus called it “the finest shot I have ever seen.”
11 / 20
Europe earned a 14-14 draw in the matches at The Belfry, retaining the cup after having won it in 1987. A key singles match for the Europeans was Christy O’Connor Jr. against Fred Couples. On paper, it appeared to be an easy point for the U.S. and the younger, stronger, longer Couples. On the final hole, however, O’Connor ripped a 5-iron to within 5 feet of the pin, then made the putt to win the match.
12 / 20
Jack Nicklaus usually gets the credit/blame for suggesting that the RyderCup expand the Great Britain and Ireland team to one representing all of Europe. Ironically, Nicklaus didn’t make the U.S. team for Europe’s coming-out party in 1979. And the only two players who were eligible because of the change, Spain’s Seve Ballesteros and Antonio Garrido, were 1-3 in team matches and 0-2 in singles as the U.S. rolled, 17-11. But the die was cast: Counting that first year, Europe is 10-7-1
13 / 20
The matches were tied, 13-13, when Lanny Wadkins and Jose Maria Canizares went to the 18th hole at PGA National with Canizares 1 up. Hitting a wedge for his third shot on the par-5 closing hole, Wadkins stuffed it to 3 feet, then made the birdie putt to win the hole and halve the match. U.S. captain Jack Nicklaus was so impressed, he kissed Wadkins’ divot as the U.S. went on to win, 14 ½ to 13 ½.
14 / 20
For most of his career, Seve Ballesteros was the most dynamic player on the European side in the Ryder Cup. His playing skills may have waned, but his fiery competitiveness and ability to inspire never did. So the 1997 Ryder Cup, to be held at Valderrama in Spain and with Ballesteros captaining the European side, was awaited with great anticipation. The results didn’t disappoint, either, as Europe took a 14 ½-to-13 ½ win.
15 / 20
At the gala dinner before the competition began in Houston, both captains introduced their squads. Dai Rees introduced the GB&I players one by one, noting their accomplishments. U.S. captain Ben Hogan simply said, “Ladies and gentlemen, the United States Ryder Cup team – the finest gofers in the world.” The U.S. went on to record the most lopsided victory in the history of the competition – 23 ½ to 8 ½.
16 / 20
The Americans suffered their first loss on home soil as Europe took a 15-13 win at Muirfield Village. Among the U.S. losers in singles was Ben Crenshaw, who broke his putter in frustration on the sixth hole and putted with a 1-iron the rest of his match with Eamonn Darcy.
17 / 20
The Ryder Cup wasn’t anything close to the monster event it is now in 1985. The U.S. hadn’t lost since 1957, but at The Belfry in Sutton Coldfield, England, Europe won by five points. Craig Stadler was the only U.S. winner in the first eight singles matches,
18 / 20
After losing for a third consecutive time in 2014, the U.S. declared the need for a "task force." Though ridiculed, things finally turned out in America's favor as Davis Love III's team won the Ryder Cup for the first time since 2008, 17-11, at Hazeltine National.
19 / 20
Boo Weekley is perhaps the biggest free spirit ever to play in a Ryder Cup. When he made the U.S team for the first (and thus far, only) time in 2008, he was excited. He happened to catch the scene in Happy Gilmore where Adam Sandler “rides the bull” after hitting a big tee shot, and decided he wanted to do it, too. So after his opening tee shot in his singles match, Weekley happily “rode the bull” down the fairway.
20 / 20
One of the most firmly held beliefs about the Ryder Cup was that no matter what happened in the team matches, the United States would dominate the singles. And that was largely true – until 1995, when Europe for the first time came from behind on the final day to win. The U.S. went into the singles with a 9-7 lead, but lost the singles, 7 ½ to 4 ½. Curtis Strange, a controversial captain’s pick by Lanny Wadkins, lost his singles match to Nick Faldo when he bogeyed the final three holes. The venue was Oak Hill, and the result was bitterly dubbed Choke Hill.