Here is the MLS schedule for the opening weekend of the 1999 season. Please note that all times are eastern.
| Date | Matchup | Kickoff | Television |
| March 20 | D.C. United at Tampa Bay | 7:00 p.m. | TBA |
| March 20 | MetroStars at Miami | 8:00 p.m. | TBA |
| March 20 | Kansas City at Dallas | 8:30 p.m. | TBA |
| March 20 | Chicago at San Jose | 11:00 p.m. | TBA |
| March 21 | Colorado at Los Angeles | 7:30 p.m. | TBA |