← Caribbean Cup Qualifying - 1999 →
- Friday, May 07, 1999
- in Bermuda
scoreboard
| ECU1 | 1999 | 12 | Delfín | 1 - 4 | Deportivo Cuenca | 1 | ||
| NED1 | 1998-1999 | 32 | Fortuna Sittard | 6 - 4 | PSV Eindhoven | 1 | ||
| BOL1 | 1999 | 17 | Club Destroyers | 2 - 2 | Guabirá | 1 | ||
| TUR1 | 1998-1999 | 31 | Antalyaspor | 1 - 2 | Samsunspor | 1 | ||
| BRA-SP | 1999 | 12 | 2 | Palmeiras | 3 - 2 | Rio Branco | 1 | |
| BRA-SP | 1999 | 12 | 2 | Barbarense | 1 - 3 | Corinthians | 1 | |
| CCQ | 1999 | Bahamas | 0 - 7 | Cuba | Bermuda | 2 |