| 2. Round | 02/04/1999 | Kansas City Wizards | - | New England Revolution | 0:1 | ||||
| 2. Round | 09/04/1999 | Kansas City Wizards | - | San Jose Clash | n.P. | ||||
| 2. Round | 16/04/1999 | Colorado Rapids | - | Kansas City Wizards | n.P. | ||||
| 2. Round | 23/04/1999 | Miami Fusion | - | Kansas City Wizards | 1:0 | ||||
| 3. Round | 21/05/1999 | Chicago Fire | - | Kansas City Wizards | 3:1 |  |
|||
| 4. Round | 05/06/1999 | Los Angeles Galaxy | - | Kansas City Wizards | 1:0 | ||||
| 4. Round | 11/06/1999 | Kansas City Wizards | - | Dallas Burn | 1:0 | ||||
| 4. Round | 25/06/1999 | D.C. United | - | Kansas City Wizards | 3:0 | ||||
| 6. Round | 13/08/1999 | MetroStars | - | Kansas City Wizards | 1:2 | |
|||
| 7. Round | 03/09/1999 | San Jose Clash | - | Kansas City Wizards | 2:0 | ||||
| 7. Round | 06/09/1999 | New England Revolution | - | Kansas City Wizards | 3:2 | ||||
| 7. Round | 09/09/1999 | Colorado Rapids | - | Kansas City Wizards | n.P. | ||||
| 7. Round | 24/09/1999 | Kansas City Wizards | - | Colorado Rapids | n.P. | ||||
| 8. Round | 05/10/1999 | San Jose Clash | - | Kansas City Wizards | 1:0 |
USA