9. 1990 Hale Irwin vs. Mike Donald
280-280 (Irwin won playoff on 19th hole)

Prior to the 1990 U.S. Open at Chicago's Medinah No. 3, Hale Irwin's public persona projected all the pizzazz of an insurance salesman. One putt shattered that perception. The 45-year-old Irwin had been awarded a special exemption to play — but he wasn't supposed to win. Then again, neither was journeyman Mike Donald. Irwin came to the final regulation hole needing a 45-foot birdie putt for a 67. Astonishingly, he rolled it in. The gallery went berserk, and unexpectedly, so did Irwin. He galloped around the green, raising his arms in joy and high-fiving spectators. Donald later tied him and even matched Irwin's 74 in the Monday playoff, but on the first extra hole Irwin became the oldest U.S. Open winner ever.