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| Last 10 games | more | |||
| 02.07.2008 | Cup Round 3 | Chicago Fire | Cleveland City Stars | 4-1 |
| 29.06.2008 | D1 MLS | Chicago Fire | San Jose Earthquake | 0-0 |
| 20.06.2008 | D1 MLS | CD Chivas USA | Chicago Fire | 2-0 |
| 15.06.2008 | D1 MLS | FC Dallas | Chicago Fire | 1-0 |
| 11.06.2008 | Cup MLS Qualifying Finals | Chicago Fire | Columbus Crew | 3-2 AET |
| 08.06.2008 | D1 MLS | Chicago Fire | DC United | 1-2 |
| 25.05.2008 | D1 MLS | New York Red Bulls | Chicago Fire | 1-5 |
| 18.05.2008 | D1 MLS | Chicago Fire | Houston Dynamo | 1-2 |
| 09.05.2008 | D1 MLS | DC United | Chicago Fire | 0-2 |
| 04.05.2008 | D1 MLS | New England Revolution | Chicago Fire | 0-3 |
| Next 10 games | more | |||
| 06.07.2008 | D1 MLS | Columbus Crew | Chicago Fire |  |
| 09.07.2008 | Cup Quarterfinal | DC United | Chicago Fire | |
| 13.07.2008 | D1 MLS | Toronto FC | Chicago Fire | |
| 20.07.2008 | D1 MLS | Real Salt Lake | Chicago Fire | |
| 28.07.2008 | D1 MLS | Chicago Fire | Kansas City Wizards | |
| 31.07.2008 | CF Club Friendly | Chicago Fire | Everton FC | |
| 03.08.2008 | D1 MLS | CD Chivas USA | Chicago Fire | |
| 10.08.2008 | D1 MLS | Chicago Fire | New England Revolution | |
| 22.08.2008 | D1 MLS | Chicago Fire | Los Angeles Galaxy | |
| 01.09.2008 | D1 MLS | Chicago Fire | Houston Dynamo | |