| 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. |  |
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| 2. Round | 16/04/1999 | Colorado Rapids | - | Kansas City Wizards | n.P. | ||||
| 2. Round | 23/04/1999 | Miami Fusion | - | Kansas City Wizards | 1:0 | ||||
| 2. Round | 27/04/1999 | Kansas City Wizards | - | Columbus Crew | 0:1 | ||||
| 3. Round | 07/05/1999 | Kansas City Wizards | - | Los Angeles Galaxy | 2:1 | ||||
| 3. Round | 14/05/1999 | Kansas City Wizards | - | D.C. United | n.P. | ||||
| 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 | 19/06/1999 | Kansas City Wizards | - | MetroStars | 6:0 | ||||
| 4. Round | 25/06/1999 | D.C. United | - | Kansas City Wizards | 3:0 | ||||
| 5. Round | 09/07/1999 | Dallas Burn | - | Kansas City Wizards | 5:0 | ||||
| 5. Round | 21/07/1999 | Kansas City Wizards | - | Tampa Bay Mutiny | 4:3 | ||||
| 5. Round | 24/07/1999 | Los Angeles Galaxy | - | Kansas City Wizards | 2:1 | ||||
| 8. Round | 08/10/1999 | Kansas City Wizards | - | Los Angeles Galaxy | 0:1 |
USA