| 6. Round | 17/08/1999 | New England Revolution | - | Tampa Bay Mutiny | 0:1 | ||||
| 6. Round | 20/08/1999 | San Jose Clash | - | New England Revolution | 2:1 | ||||
| 6. Round | 24/08/1999 | MetroStars | - | New England Revolution | n.P. | ||||
| 7. Round | 10/09/1999 | Miami Fusion | - | New England Revolution | n.P. | ||||
| 7. Round | 17/09/1999 | New England Revolution | - | Columbus Crew | n.P. |  |
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| 7. Round | 23/09/1999 | New England Revolution | - | Dallas Burn | 0:1 | ||||
| 8. Round | 01/10/1999 | New England Revolution | - | MetroStars | 2:1 | ||||
| 8. Round | 08/10/1999 | D.C. United | - | New England Revolution | n.P. |
Colombia