Quarterfinals
September 28, and 29, 1999
| Team 1 | Score | Team 2 |
|---|---|---|
| Chicago Fire | 2 - 0 | Joe Public F.C. |
| Toluca | 0 - 1 | L.D. Alajuelense |
| D.C. United | 1 - 0 | Club Deportivo Olimpia |
| Club Necaxa | 0 - 0 5-3 (pen.) |
Saprissa |
- Chicago Fire, L.D. Alajuelense, D.C. United and Club Necaxa advance to the semi-finals.
Read more about this topic: 1999 CONCACAF Champions' Cup