Chicago Fire SC 
| 1999-03-20 | MLS | San Jose Earthquakes | (A) | 3 | - 1 | W | |
| 1999-03-27 | MLS | Sporting Kansas City | (A) | 3 | - 0 | W | |
| 1999-04-03 | MLS | Miami Fusion | (A) | 4 | - 1 | W | |
| 1999-04-10 | MLS | FC Dallas | (H) | 0 | - 0 | D | |
| 1999-04-17 | MLS | Los Angeles Galaxy | (H) | 1 | - 0 | W | |
| 1999-05-01 | MLS | D.C. United | (H) | 3 | - 2 | W | |
| 1999-05-08 | MLS | Tampa Bay Mutiny | (A) | 1 | - 1 | D | |
| 1999-05-16 | MLS | Colorado Rapids | (H) | 0 | - 1 | L | |
| 1999-05-22 | MLS | Sporting Kansas City | (H) | 3 | - 1 | W | |
| 1999-05-29 | MLS | D.C. United | (A) | 1 | - 3 | L | |
| 1999-06-05 | MLS | New England Revolution | (A) | 0 | - 2 | L | |
| 1999-06-12 | MLS | Los Angeles Galaxy | (A) | 1 | - 2 | L | |
| 1999-06-19 | MLS | San Jose Earthquakes | (H) | 2 | - 0 | W | |
| 1999-06-26 | MLS | Colorado Rapids | (A) | 0 | - 2 | L | |
| 1999-07-02 | MLS | FC Dallas | (H) | 1 | - 1 | D | |
| 1999-07-04 | MLS | FC Dallas | (A) | 2 | - 1 | W | |
| 1999-07-10 | MLS | New York Red Bulls | (H) | 2 | - 0 | W | |
| 1999-07-23 | MLS | San Jose Earthquakes | (H) | 2 | - 2 | D | |
| 1999-07-31 | MLS | Los Angeles Galaxy | (H) | 0 | - 1 | L | |
| 1999-08-05 | MLS | Sporting Kansas City | (A) | 2 | - 1 | W | |
| 1999-08-08 | MLS | Colorado Rapids | (H) | 5 | - 0 | W | |
| 1999-08-14 | MLS | Miami Fusion | (H) | 1 | - 1 | D | |
| 1999-08-22 | MLS | FC Dallas | (A) | 3 | - 3 | D | |
| 1999-08-25 | MLS | Sporting Kansas City | (H) | 2 | - 0 | W | |
| 1999-08-28 | MLS | New England Revolution | (H) | 2 | - 1 | W | |
| 1999-09-05 | MLS | New York Red Bulls | (A) | 2 | - 1 | W | |
| 1999-09-11 | MLS | Los Angeles Galaxy | (A) | 0 | - 1 | L | |
| 1999-09-17 | MLS | Tampa Bay Mutiny | (H) | 1 | - 1 | D | |
| 1999-09-23 | MLS | Columbus Crew | (H) | 1 | - 2 | L | |
| 1999-09-26 | MLS | San Jose Earthquakes | (A) | 0 | - 2 | L | |
| 1999-10-06 | MLS | Colorado Rapids | (A) | 1 | - 0 | W | |
| 1999-10-10 | MLS | Columbus Crew | (A) | 2 | - 2 | D |