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| 1st(1st leg) | Estudiantes de Mérida | - | CSA - AL | 0:0 (0:0) | ||
| 2nd (2nd leg) | CSA - AL | - | Estudiantes de Mérida | 3:1 (2:1) | ||
| 1st(1st leg): 03/11/1999 23:00 | 2nd (2nd leg): 10/11/1999 00:00 | Winner: CSA - AL | ||||
| 1st(1st leg) | Sport Boys | - | São Raimundo - AM | 1:1 (1:1) | ||
| 2nd (2nd leg) | São Raimundo - AM | - | Sport Boys | 4:0 (0:0) | ||
| 1st(1st leg): 03/11/1999 23:30 | 2nd (2nd leg): 09/11/1999 23:30 | Winner: São Raimundo - AM | ||||
| 1st(1st leg) | Talleres de Córdoba | - | Paraná Clube | 1:0 (1:0) | ||
| 2nd (2nd leg) | Paraná Clube | - | Talleres de Córdoba | 1:3 (0:0, 1:0, 1:0) pso | ||
| 1st(1st leg): 04/11/1999 00:30 | 2nd (2nd leg): 10/11/1999 00:45 | Winner: Talleres de Córdoba | ||||
