Wednesday, August 16
| Year | Result |
| 1996 | Mark Brooks def. Kenny Perry on the first playoff hole at Valhalla |
| 1995 | Steve Elkington def. Colin Montgomerie on the first playoff hole at Riviera |
| 1993 | Paul Azinger def. Greg Norman on the second playoff hole at Inverness |
| 1987 | Larry Nelson def. Lanny Wadkins on the first playoff hole at PGA National |
| 1979 | David Graham def. Ben Crenshaw on the third playoff hole at Oakland Hills |
| 1978 | John Mahaffey def. Jerry Pate and Tom Watson on the second playoff hole at Oakmont |
| 1977 | Lanny Wadkins def. Gene Littler on the third playoff hole at Pebble Beach |
| 1967 | Don January (69) def. Don Massengale (71) at Columbine |
| 1961 | Jerry Barber (67) def. Don January (68) at Olympia Fields |
| 1941 | Vic Ghezzi def. Byron Nelson, 1-up, 38 holes, at Cherry Hills |
| 1939 | Henry Picard def. Byron Nelson, 1-up, 37 holes, at Pomonok |
| 1937 | Denny Shute def. Harold McSpaden, 1-up, 37 holes, at Pittsburgh |
| 1934 | Paul Runyan def. Craig Wood, 1-up, 38 holes, at Park Club of Buffalo |
| 1923 | Gene Sarazen def. Walter Hagen, 1-up, 38 holes, at Pelham |
| Note: | The PGA switched from match play to stroke play in 1958. A sudden-death playoff format began in 1977 |
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