Here is the 1999 Columbus Crew schedule. Please note that all times are ET and that the schedule is subject to change.
| Date | Opponent | Time (ET) |
| Sun. March 28 | at MetroStars | 1:00 p.m. |
| Sat. April 3 | at Tampa Bay | 7:00 p.m. |
| Thu. April 8 | at Los Angeles | 10:30 p.m. |
| Sat. April 17 | at New England | 7:30 p.m. |
| Sat. April 24 | at Dallas | 8:30 p.m. |
| Wed. April 28 | at Kansas City | 12:30 p.m. |
| Sun. May 9 | at San Jose | 5:00 p.m. |
| Sat. May 15 | New England | 7:30 p.m. |
| Sat. May 22 | Tampa Bay | 7:30 p.m. |
| Sat. May 29 | Los Angeles | 7:30 p.m. |
| Sat. June 5 | at D.C. United | 7:30 p.m. |
| Sun. June 13 | D.C. United | 4:00 p.m. |
| Wed. June 16 | New England | 7:30 p.m. |
| Sat. June 26 | MetroStars | 7:30 p.m. |
| Wed. June 30 | San Jose | 7:30 p.m. |
| Sun. July 4 | at Colorado | 9:00 p.m. |
| Wed. July 7 | D.C. United | 7:30 p.m. |
| Sat. July 10 | at Miami | 7:30 p.m. |
| Sat. July 24 | Dallas | 7:30 p.m. |
| Sun. Aug. 1 | Miami | 1:00 p.m. |
| Sun. Aug. 8 | Kansas City | 6:00 p.m. |
| Sat. Aug. 14 | at D.C. United | 4:00 p.m. |
| Wed. Aug. 18 | at MetroStars | 7:00 p.m. |
| Sun. Aug. 22 | Tampa Bay | 4:00 p.m. |
| Fri. Aug. 27 | at Tampa Bay | 7:30 p.m. |
| Sat. Sept. 4 | Colorado | 7:30 p.m. |
| Sun. Sept. 12 | MetroStars | 1:00 p.m. |
| Sat. Sept. 18 | at New England | 7:30 p.m. |
| Thu. Sept. 23 | at Chicago | 8:00 p.m. |
| Sun. Sept. 26 | Miami | 1:00 p.m. |
| Sun. Oct. 3 | at Miami | 7:30 p.m. |
| Sun. Oct. 10 | Chicago | 1:00 p.m. |