Chicago Fire SC 
| 2000-03-18 | MLS | FC Dallas | (A) | 2 | - 4 | L | |
| 2000-03-25 | MLS | Sporting Kansas City | (A) | 3 | - 4 | L | |
| 2000-04-01 | MLS | Columbus Crew | (A) | 2 | - 0 | W | |
| 2000-04-08 | MLS | D.C. United | (A) | 2 | - 3 | L | |
| 2000-04-15 | MLS | Miami Fusion | (H) | 1 | - 0 | W | |
| 2000-04-22 | MLS | New England Revolution | (A) | 1 | - 1 | D | |
| 2000-04-28 | MLS | Tampa Bay Mutiny | (H) | 5 | - 1 | W | |
| 2000-05-03 | MLS | Colorado Rapids | (H) | 1 | - 2 | L | |
| 2000-05-06 | MLS | Miami Fusion | (A) | 3 | - 0 | W | |
| 2000-05-13 | MLS | San Jose Earthquakes | (H) | 4 | - 1 | W | |
| 2000-05-20 | MLS | New England Revolution | (H) | 0 | - 1 | L | |
| 2000-05-24 | MLS | FC Dallas | (H) | 4 | - 3 | W | |
| 2000-05-27 | MLS | New York Red Bulls | (A) | 1 | - 4 | L | |
| 2000-06-04 | MLS | Sporting Kansas City | (H) | 3 | - 2 | W | |
| 2000-06-07 | MLS | Miami Fusion | (H) | 2 | - 1 | W | |
| 2000-06-10 | MLS | Miami Fusion | (A) | 2 | - 4 | L | |
| 2000-06-17 | MLS | D.C. United | (H) | 3 | - 2 | W | |
| 2000-06-21 | MLS | Los Angeles Galaxy | (A) | 1 | - 1 | D | |
| 2000-06-24 | MLS | San Jose Earthquakes | (A) | 1 | - 1 | D | |
| 2000-07-04 | MLS | Colorado Rapids | (A) | 1 | - 2 | L | |
| 2000-07-08 | MLS | Columbus Crew | (H) | 3 | - 1 | W | |
| 2000-07-15 | MLS | Tampa Bay Mutiny | (H) | 0 | - 0 | D | |
| 2000-07-21 | MLS | Colorado Rapids | (A) | 1 | - 1 | D | |
| 2000-08-02 | MLS | Tampa Bay Mutiny | (A) | 1 | - 0 | W | |
| 2000-08-06 | MLS | New York Red Bulls | (H) | 3 | - 1 | W | |
| 2000-08-16 | MLS | FC Dallas | (A) | 0 | - 3 | L | |
| 2000-08-19 | MLS | Los Angeles Galaxy | (H) | 2 | - 1 | W | |
| 2000-08-26 | MLS | Tampa Bay Mutiny | (A) | 3 | - 3 | D | |
| 2000-08-30 | MLS | FC Dallas | (H) | 4 | - 0 | W | |
| 2000-09-03 | MLS | Colorado Rapids | (H) | 2 | - 1 | W | |
| 2000-09-06 | MLS | Columbus Crew | (H) | 3 | - 1 | W | |
| 2000-09-09 | MLS | Columbus Crew | (A) | 3 | - 2 | W |