| 2. Round | 18/05/2001 | Chicago Fire | - | Kansas City Wizards | 2:0 | ||||
| 2. Round | 25/05/2001 | Chicago Fire | - | San Jose Earthquakes | 1:1 aet | ||||
| 2. Round | 29/05/2001 | Chicago Fire | - | Los Angeles Galaxy | 3:4 | ||||
| 3. Round | 08/06/2001 | Chicago Fire | - | Columbus Crew | 1:0 | ||||
| 3. Round | 22/06/2001 | Chicago Fire | - | New England Revolution | 1:1 aet |  |
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| 3. Round | 29/06/2001 | Chicago Fire | - | MetroStars | 3:1 | ||||
| 4. Round | 03/07/2001 | Kansas City Wizards | - | Chicago Fire | 0:7 |  |
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| 4. Round | 06/07/2001 | Tampa Bay Mutiny | - | Chicago Fire | 2:3 | ||||
| 4. Round | 13/07/2001 | Chicago Fire | - | Colorado Rapids | 1:0 aet | |
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| 4. Round | 17/07/2001 | Miami Fusion | - | Chicago Fire | 2:1 | |
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| 4. Round | 20/07/2001 | Chicago Fire | - | Dallas Burn | 2:1 aet | ||||
| 5. Round | 17/08/2001 | San Jose Earthquakes | - | Chicago Fire | 0:1 | ||||
| 6. Round | 31/08/2001 | MetroStars | - | Chicago Fire | 0:1 aet | |
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| 6. Round | 07/09/2001 | Chicago Fire | - | Dallas Burn | 2:2 aet |
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