| 1. Round | 19/03/1999 | Tampa Bay Mutiny | - | D.C. United | 2:5 | ||||
| 2. Round | 02/04/1999 | Tampa Bay Mutiny | - | Columbus Crew | 2:3 | ||||
| 2. Round | 10/04/1999 | Tampa Bay Mutiny | - | MetroStars | n.P. | ||||
| 2. Round | 17/04/1999 | Dallas Burn | - | Tampa Bay Mutiny | 2:1 | ||||
| 2. Round | 24/04/1999 | MetroStars | - | Tampa Bay Mutiny | 0:1 | ||||
| 3. Round | 30/04/1999 | Tampa Bay Mutiny | - | Miami Fusion | 2:1 | ||||
| 3. Round | 07/05/1999 | Tampa Bay Mutiny | - | Chicago Fire | n.P. | ||||
| 3. Round | 14/05/1999 | Los Angeles Galaxy | - | Tampa Bay Mutiny | n.P. | ||||
| 3. Round | 21/05/1999 | Columbus Crew | - | Tampa Bay Mutiny | n.P. | ||||
| 3. Round | 28/05/1999 | Miami Fusion | - | Tampa Bay Mutiny | 2:1 |  |
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| 4. Round | 04/06/1999 | Tampa Bay Mutiny | - | Miami Fusion | 1:0 | ||||
| 4. Round | 11/06/1999 | San Jose Clash | - | Tampa Bay Mutiny | n.P. | ||||
| 4. Round | 18/06/1999 | Tampa Bay Mutiny | - | New England Revolution | 2:3 | ||||
| 4. Round | 26/06/1999 | Tampa Bay Mutiny | - | Los Angeles Galaxy | 2:4 | ||||
| 4. Round | 29/06/1999 | MetroStars | - | Tampa Bay Mutiny | n.P. | |
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| 5. Round | 02/07/1999 | Tampa Bay Mutiny | - | Kansas City Wizards | n.P. | ||||
| 5. Round | 07/07/1999 | Tampa Bay Mutiny | - | San Jose Clash | 2:1 |
USA