1. Round | 17/03/2000 | Dallas Burn | - | Chicago Fire | 4:2 | ||||
1. Round | 24/03/2000 | Kansas City Wizards | - | Chicago Fire | 4:3 | ||||
2. Round | 31/03/2000 | Columbus Crew | - | Chicago Fire | 0:2 | ![]() |
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2. Round | 07/04/2000 | D.C. United | - | Chicago Fire | 3:2 | ||||
2. Round | 14/04/2000 | Chicago Fire | - | Miami Fusion | 1:0 | ||||
2. Round | 21/04/2000 | New England Revolution | - | Chicago Fire | 1:1 aet | ![]() |
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2. Round | 27/04/2000 | Chicago Fire | - | Tampa Bay Mutiny | 5:1 | ![]() |
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3. Round | 02/05/2000 | Chicago Fire | - | Colorado Rapids | 1:2 | ![]() |
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3. Round | 05/05/2000 | Miami Fusion | - | Chicago Fire | 0:3 | ![]() |
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3. Round | 12/05/2000 | Chicago Fire | - | San Jose Earthquakes | 4:1 | ![]() |
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3. Round | 19/05/2000 | Chicago Fire | - | New England Revolution | 0:1 | ||||
6. Round | 01/08/2000 | Tampa Bay Mutiny | - | Chicago Fire | 0:1 | ![]() |
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6. Round | 05/08/2000 | Chicago Fire | - | MetroStars | 3:1 |