| Day | Match |
USA
|
EUROPE
|
Result |
|---|---|---|---|---|
| 1999 - USA Win 14.5 - 13.5 | ||||
| 1 | Fourballs | Jim Furyk / Phil Mickelson | Sergio Garcia / Jesper Parnevik | 1 up |
| 1 | Fourballs | Justin Leonard / Davis Love III | Colin Montgomerie / Paul Lawrie | halved |
| 1 | Fourballs | Jeff Maggert / Hal Sutton | Miguel Angel Jimenez / Jose Maria Olazabal | 2 & 1 |
| 1 | Fourballs | David Duval / Tiger Woods | Darren Clarke / Lee Westwood | 1 up |
| 1 | Foursomes | David Duval / Phil Mickelson | Paul Lawrie / Colin Montgomerie | 3 & 2 |
| 1 | Foursomes | Tom Lehman / Tiger Woods | Sergio Garcia / Jesper Parnevik | 2 & 1 |
| 1 | Foursomes | Davis Love III / Payne Stewart | Padraig Harrington / Miguel Angel Jimenez | halved |
| 1 | Foursomes | Jeff Maggert / Hal Sutton | Darren Clarke / Lee Westwood | 3 & 2 |
| 2 | Fourballs | Phil Mickelson / Tom Lehman | Darren Clarke / Lee Westwood | 2 & 1 |
| 2 | Fourballs | Davis Love III / David Duval | Sergio Garcia / Jesper Parnevik | halved |
| 2 | Fourballs | Justin Leonard / Hal Sutton | Miguel Angel Jimenez / Jose Maria Olazabal | halved |
| 2 | Fourballs | Steve Pate / Tiger Woods | Paul Lawrie / Colin Montgomerie | 2 & 1 |
| 2 | Foursomes | Jeff Maggert / Hal Sutton | Colin Montgomerie / Paul Lawrie | 3 & 2 |
| 2 | Foursomes | Jim Furyk / Mark O'Meara | Darren Clarke / Lee Westwood | 1 up |
| 2 | Foursomes | Steve Pate / Tiger Woods | Miguel Angel Jimenez / Padraig Harrington | 1 up |
| 2 | Foursomes | Justin Leonard / Payne Stewart | Sergio Garcia / Jesper Parnevik | 3 & 2 |
| 3 | Singles | Tom Lehman | Lee Westwood | 3 & 2 |
| 3 | Singles | Davis Love III | Jean Van de Velde | 6 & 5 |
| 3 | Singles | Phil Mickelson | Jarmo Sandelin | 4 & 3 |
| 3 | Singles | Hal Sutton | Darren Clarke | 4 & 2 |
| 3 | Singles | David Duval | Jesper Parnevik | 5 & 4 |
| 3 | Singles | Tiger Woods | Andrew Coltart | 3 & 2 |
| 3 | Singles | Steve Pate | Miguel Angel Jimenez | 2 & 1 |
| 3 | Singles | Mark O'Meara | Padraig Harrington | 1 up |
| 3 | Singles | Jim Furyk | Sergio Garcia | 4 & 3 |
| 3 | Singles | Jeff Maggert | Paul Lawrie | 4 & 3 |
| 3 | Singles | Justin Leonard | Jose Maria Olazabal | halved |
| 3 | Singles | Payne Stewart | Colin Montgomerie | 1 up |
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