| 20-dic-1999 | Sausalito | Everton | 1 | Riep |
| Iquique | 0 | |||
| 23-dic-1999 | Iquique | Iquique | 0 | |
| Everton | 1 | Pereyra | ||
| 20-dic-1999 | Parque Schott | Osorno | 4 | Muñoz (P), Olea (2), Soto |
| Cobresal | 3 | Retamal, Núñez, Donoso | ||
| 23-dic-1999 | El Cobre | Cobresal | 2 | Cisternas, Núñez |
| Osorno | 3 | Olea, Díaz, Muñoz | ||
| Ganadores: Everton y Osorno | ||||