| 4. Round | 02/06/2000 | Dallas Burn | - | Tampa Bay Mutiny | 2:3 | ||||
| 4. Round | 08/06/2000 | MetroStars | - | Tampa Bay Mutiny | 0:3 | ||||
| 4. Round | 23/06/2000 | Miami Fusion | - | Tampa Bay Mutiny | 2:3 | ||||
| 4. Round | 27/06/2000 | Columbus Crew | - | Tampa Bay Mutiny | 1:2 | ||||
| 5. Round | 30/06/2000 | Tampa Bay Mutiny | - | MetroStars | 0:2 | ||||
| 5. Round | 03/07/2000 | Tampa Bay Mutiny | - | D.C. United | 3:0 | ||||
| 5. Round | 11/07/2000 | D.C. United | - | Tampa Bay Mutiny | 2:2 aet |  |
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| 5. Round | 14/07/2000 | Chicago Fire | - | Tampa Bay Mutiny | 0:0 aet | ||||
| 5. Round | 21/07/2000 | Tampa Bay Mutiny | - | Los Angeles Galaxy | 2:0 | ||||
| 6. Round | 04/08/2000 | Tampa Bay Mutiny | - | Dallas Burn | 2:1 | ||||
| 6. Round | 15/08/2000 | Tampa Bay Mutiny | - | MetroStars | 4:3 aet | ||||
| 6. Round | 25/08/2000 | Tampa Bay Mutiny | - | Chicago Fire | 3:3 aet | ||||
| 6. Round | 29/08/2000 | Columbus Crew | - | Tampa Bay Mutiny | 3:4 | ||||
| 7. Round | 08/09/2000 | Tampa Bay Mutiny | - | Kansas City Wizards | 2:2 aet |
USA