Columbus Crew 
| 1999-03-28 | MLS | New York Red Bulls | (A) | 0 | - 1 | L | |
| 1999-04-03 | MLS | Tampa Bay Mutiny | (A) | 3 | - 2 | W | |
| 1999-04-08 | MLS | Los Angeles Galaxy | (A) | 1 | - 1 | D | |
| 1999-04-17 | MLS | New England Revolution | (A) | 0 | - 0 | D | |
| 1999-04-24 | MLS | FC Dallas | (A) | 0 | - 2 | L | |
| 1999-04-28 | MLS | Sporting Kansas City | (A) | 1 | - 0 | W | |
| 1999-05-09 | MLS | San Jose Earthquakes | (A) | 2 | - 1 | W | |
| 1999-05-15 | MLS | New England Revolution | (H) | 2 | - 0 | W | |
| 1999-05-22 | MLS | Tampa Bay Mutiny | (H) | 0 | - 0 | D | |
| 1999-05-29 | MLS | Los Angeles Galaxy | (H) | 1 | - 1 | D | |
| 1999-06-05 | MLS | D.C. United | (A) | 0 | - 1 | L | |
| 1999-06-13 | MLS | D.C. United | (H) | 1 | - 2 | L | |
| 1999-06-16 | MLS | New England Revolution | (H) | 1 | - 1 | D | |
| 1999-06-26 | MLS | New York Red Bulls | (H) | 2 | - 1 | W | |
| 1999-06-30 | MLS | San Jose Earthquakes | (H) | 3 | - 3 | D | |
| 1999-07-04 | MLS | Colorado Rapids | (A) | 3 | - 0 | W | |
| 1999-07-07 | MLS | D.C. United | (H) | 1 | - 1 | D | |
| 1999-07-10 | MLS | Miami Fusion | (A) | 0 | - 2 | L | |
| 1999-07-24 | MLS | FC Dallas | (H) | 4 | - 1 | W | |
| 1999-08-01 | MLS | Miami Fusion | (H) | 4 | - 0 | W | |
| 1999-08-08 | MLS | Sporting Kansas City | (H) | 2 | - 1 | W | |
| 1999-08-14 | MLS | D.C. United | (A) | 1 | - 2 | L | |
| 1999-08-18 | MLS | New York Red Bulls | (A) | 4 | - 2 | W | |
| 1999-08-22 | MLS | Tampa Bay Mutiny | (H) | 1 | - 1 | D | |
| 1999-08-27 | MLS | Tampa Bay Mutiny | (A) | 1 | - 2 | L | |
| 1999-09-04 | MLS | Colorado Rapids | (H) | 2 | - 1 | W | |
| 1999-09-12 | MLS | New York Red Bulls | (H) | 1 | - 2 | L | |
| 1999-09-18 | MLS | New England Revolution | (A) | 0 | - 0 | D | |
| 1999-09-23 | MLS | Chicago Fire SC | (A) | 2 | - 1 | W | |
| 1999-09-26 | MLS | Miami Fusion | (H) | 2 | - 1 | W | |
| 1999-10-03 | MLS | Miami Fusion | (A) | 1 | - 4 | L | |
| 1999-10-10 | MLS | Chicago Fire SC | (H) | 2 | - 2 | D |