| 5. Round | 21/07/1999 | Kansas City Wizards | - | Tampa Bay Mutiny | 4:3 |  |
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| 5. Round | 24/07/1999 | Colorado Rapids | - | Tampa Bay Mutiny | n.P. | ||||
| 5. Round | 28/07/1999 | Miami Fusion | - | Tampa Bay Mutiny | n.P. | |
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| 5. Round | 30/07/1999 | Tampa Bay Mutiny | - | New England Revolution | 4:1 | |
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| 6. Round | 07/08/1999 | D.C. United | - | Tampa Bay Mutiny | n.P. | ||||
| 6. Round | 12/08/1999 | Tampa Bay Mutiny | - | Colorado Rapids | 0:1 | ||||
| 7. Round | 24/09/1999 | Tampa Bay Mutiny | - | MetroStars | 1:2 | ||||
| 8. Round | 05/10/1999 | D.C. United | - | Tampa Bay Mutiny | 2:4 | ||||
| 8. Round | 09/10/1999 | Tampa Bay Mutiny | - | Dallas Burn | 1:2 |
USA