33rd Ryder Cup at The Country Club, Brookline, Massachusetts from 24th - 27th September
| The Country Club, Brookline, Massachusetts. September 24th to 26th 1999 |
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| Europe Captain: Mark James | America Captain: Ben Crenshaw | |||||
| Europe | Holes | Points | America | Holes | Points | |
| Foursomes a.m. Sept. 24 | ||||||
| C. Montgomerie & P. Lawrie | 3 & 2 | 1 | D. Duval & P. Mickelson | 0 | ||
| J. Parnevik & S. Garcia | 2 & 1 | 1 | T. Lehman & T. Woods | 0 | ||
| M. A. Jimenez & P. Harrington | halved | ½ | D. Love III & Stewart | halved | ½ | |
| D. Clarke & L. Westwood | 0 | H. Sutton & J. Maggert | 3 & 2 | 1 | ||
| Fourball p.m. Sept 24 | ||||||
| C. Montgomerie & P. Lawrie | halved | ½ | D. Love III & J. Leonard | halved | ½ | |
| J. Parnevik & S. Garcia | 1-up | 1 | P. Mickelson & J. Furyk | 0 | ||
| M.A.Jimenez & J.M.Olazabal | 2 & 1 | 1 | H. Sutton & J. Maggert | 0 | ||
| D. Clarke & L. Westwood | 1-up | 1 | D. Duval & T. Woods | 0 | ||
| Total Points after Day 1 | 6 | 2 | ||||
| Foursomes a.m. Sept. 25 | ||||||
| C. Montgomerie & P. Lawrie | 0 | H. Sutton & J. Maggert | 1-up | 1 | ||
| D. Clarke & L. Westwood | 3 & 2 | 1 | J. Furyk & M. O'Meara | 0 | ||
| M. A. Jimenez & P. Harrington | 0 | S. Pate & T. Woods | 1-up | 1 | ||
| J. Parnevik & S. Garcia | 3 & 2 | 1 | P. Stewart & J. Leonard | 0 | ||
| Fourball p.m Sept. 25 | ||||||
| D. Clarke & L. Westwood | 0 | P. Mickelson & T. Lehman | 2 & 1 | 1 | ||
| J. Parnevik & S. Garcia | halved | ½ | D. Love III & D. Duval | halved | ½ | |
| M.A.Jimenez & J.M.Olazabal | halved | ½ | J. Leonard & H. Sutton | halved | ½ | |
| C. Montgomerie & P. Lawrie | 2 & 1 | 1 | S. Pate & T. Woods | 0 | ||
| Total Points after Day 2 | 10 | 6 | ||||
| Singles Sept. 26 | ||||||
| Lee Westwood | 0 | Tom Lehman | 3 & 2 | 1 | ||
| Darren Clarke | 0 | Hal Sutton | 4 & 2 | 1 | ||
| Jarmo. Sandelin | 0 | Phil Mickelson | 4 & 3 | 1 | ||
| Jan Van de Valde | 0 | Davis Love III | 6 & 5 | 1 | ||
| Andrew Coltart | 0 | Tiger Woods | 3 & 2 | 1 | ||
| Jesper Parnevik | 0 | David Duval | 5 & 4 | 1 | ||
| Padraig Harrington | 1-up | 1 | Mark O'Meara | 0 | ||
| Miguel Angel Jimenez | 0 | Steve Pate | 2 & 1 | 1 | ||
| Jose Maria Olazabal | halved | ½ | Justin Leonard | halved | ½ | |
| Colin Montgomerie | 1-up | 1 | Payne Stewart | 0 | ||
| Sergio Garcia | 0 | Jim Furyk | 4 & 3 | 1 | ||
| Paul Lawrie | 4 & 3 | 1 | Jeff Maggert | 0 | ||
| Total Points after Day 3 | 13 ½ | 14 ½ | ||||