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 | ||||
3. Round | 07/05/1999 | Tampa Bay Mutiny | - | Chicago Fire | 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 | ||||
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 | ||||
5. Round | 21/07/1999 | Kansas City Wizards | - | Tampa Bay Mutiny | 4:3 | ||||
5. Round | 24/07/1999 | Colorado Rapids | - | Tampa Bay Mutiny | n.P. | ||||
5. Round | 28/07/1999 | Miami Fusion | - | Tampa Bay Mutiny | n.P. | ||||
5. Round | 30/07/1999 | Tampa Bay Mutiny | - | New England Revolution | 4:1 | ||||
7. Round | 03/09/1999 | New England Revolution | - | Tampa Bay Mutiny | 1:5 | ||||
7. Round | 16/09/1999 | Chicago Fire | - | Tampa Bay Mutiny | n.P. | ||||
7. Round | 24/09/1999 | Tampa Bay Mutiny | - | MetroStars | 1:2 | ||||
8. Round | 09/10/1999 | Tampa Bay Mutiny | - | Dallas Burn | 1:2 |