Semifinals
October 1, 1999
| Team 1 | Score | Team 2 |
|---|---|---|
| Chicago Fire | 1 - 1 4 - 5 (pen) |
L.D. Alajuelense |
| D.C. United | 1 - 3 | Club Necaxa |
- L.D. Alajuelense and Necaxa advance to the Final.
Read more about this topic: 1999 CONCACAF Champions' Cup
Semifinals
October 1, 1999
| Team 1 | Score | Team 2 |
|---|---|---|
| Chicago Fire | 1 - 1 4 - 5 (pen) |
L.D. Alajuelense |
| D.C. United | 1 - 3 | Club Necaxa |
Read more about this topic: 1999 CONCACAF Champions' Cup