1999: Pinehurst No. 2
Lost by 1 to Payne Stewart
Breaking Point: With a bogey on the 489-yard, par-4 16th hole (Stewart made a 25-foot par putt), Mickelson lost his lead. He and Stewart both knocked tee shots inside 10 feet on the par-3 17th, but only Stewart made his (three-foot) birdie putt. Mickelson's caddie, Jim Mackay, has since said he misread Phil's eight-footer.
2 of 5Mark Lennihan/AP
2002: Bethpage Black
Lost by 3 to Tiger Woods
Breaking Point: This was always Tiger's week, but after Mickelson birdied the par-5 13th hole he closed the gap to two strokes. Alas, Mickelson, playing on his 32nd birthday, had no chance after making bogey at 16. Woods would win easily despite making bogeys on two of his last three holes in near darkness.
3 of 5J. Conrad Williams Jr./Newsday/Abaca
2004: Shinnecock Hills
Lost by 2 to Retief Goosen
Breaking Point: Mickelson birdied the par-5 16th hole to take the lead, but his 6-iron tee shot found the left bunker on the par-3 17th and his sand shot came out hot and wound up eight feet above the hole. Mickelson's par putt missed the cup and rolled six feet by and he missed the next one for a crushing double-bogey.
4 of 5Michael Conroy/AP
2006: Winged Foot
Lost by 1 to Geoff Ogilvy
Breaking Point: Mickelson drove his final tee shot off a hospitality tent and double-bogeyed, part of a horrific pile-up on 18 that also included Colin Montgomerie (double), Jim Furyk (missed five-foot par putt), and Padraig Harrington (triple on Saturday), and that sent the trophy home with Ogilvy.
5 of 5Chris McGrath/Getty Images
2009: Bethpage Black
Lost by 2 to Lucas Glover
Breaking Point: Things looked good when Mickelson birdied 12 and eagled 13 to take the lead, but an ill-timed three-putt did him in yet again. On 15 Mickelson hit a badly misjudged first putt and then missed his par putt. He also bogeyed the par-3 17th hole, and when Glover made his only birdie of the day on 16, it was over.
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