| Campeonato Primera División "B" 1999 | ||||
| 1º Fase | ||||
| Zona Norte | ||||
| 1º Fecha | ||||
| 27-feb-1999 | Arica | Arica | 2 | Fre, Candia | 
| Wanderers | 0 | |||
| 27-feb-1999 | Ovalle | Ovalle | 1 | Salinas | 
| Magallanes | 0 | |||
| 28-feb-1999 | Sausalito | Everton | 1 | Romero (P) | 
| Antofagasta | 1 | Molina | ||
| 28-feb-1999 | Melipilla | Melipilla | 1 | Osorio | 
| San Felipe | 1 | Ojeda | ||
| 2º Fecha | ||||
| 6-mar-1999 | Arica | Arica | 1 | Rojas | 
| Everton | 0 | |||
| 7-mar-1999 | Maipú | Magallanes | 2 | R. Olivares, López | 
| Melipilla | 0 | |||
| 7-mar-1999 | Playa Ancha | Wanderers | 3 | Avila, Naif, Navia | 
| Ovalle | 0 | |||
| 7-mar-1999 | San Felipe | San Felipe | 3 | Ceballos, Figueroa (2) | 
| Antofagasta | 1 | Cabezas | ||
| 3º Fecha | ||||
| 13-mar-1999 | Ovalle | Ovalle | 0 | |
| Arica | 0 | |||
| 14-mar-1999 | Melipilla | Melipilla | 2 | Osorio (P), Pérez | 
| Wanderers | 2 | Navia, Villarroel | ||
| 14-mar-1999 | Antofagasta | Antofagasta | 0 | |
| Magallanes | 1 | Dwingelo | ||
| 14-mar-1999 | Sausalito | Everton | 2 | Pereyra, Arancibia | 
| San Felipe | 0 | |||
| 4º Fecha | ||||
| 20-mar-1999 | Ovalle | Ovalle | 0 | |
| Everton | 1 | Romero | ||
| 20-mar-1999 | Arica | Arica | 2 | Avilés, Rojas | 
| Melipilla | 0 | |||
| 21-mar-1999 | Maipú | Magallanes | 1 | Dwingelo | 
| San Felipe | 0 | |||
| 21-mar-1999 | Playa Ancha | Wanderers | 3 | J. Pérez (2, 1P), A. González | 
| Antofagasta | 2 | Cussó, Molina | ||
| 5º Fecha | ||||
| 28-mar-1999 | Sausalito | Everton | 3 | Hörmann (2), Pereyra | 
| Magallanes | 2 | Correa, C. Olivares | ||
| 28-mar-1999 | Melipilla | Melipilla | 5 | Villán (2), Arenas, Osorio (2) | 
| Ovalle | 0 | |||
| 28-mar-1999 | San Felipe | San Felipe | 2 | González, Durán | 
| Wanderers | 3 | Navia (2), J. Pérez (P) | ||
| 28-mar-1999 | Antofagasta | Antofagasta | 1 | Molina (P) | 
| Arica | 1 | Fre | ||
| 6º Fecha | ||||
| 3-abr-1999 | Arica | Arica | 2 | Tello, Fre | 
| San Felipe | 3 | Fuentes, Rubio (P), Ceballos | ||
| 3-abr-1999 | Ovalle | Ovalle | 3 | Salinas, Aliaga, Cortés | 
| Antofagasta | 1 | Molina | ||
| 4-abr-1999 | Melipilla | Melipilla | 0 | |
| Everton | 2 | Arancibia, Romero (P) | ||
| 4-abr-1999 | Playa Ancha | Wanderers | 1 | Navia | 
| Magallanes | 1 | Rojas | ||
| 7º Fecha | ||||
| 10-abr-1999 | Antofagasta | Antofagasta | 3 | Zamora, Pino (P), Molina | 
| Melipilla | 2 | Armijo, Solís | ||
| 11-abr-1999 | San Felipe | San Felipe | 1 | Reyes | 
| Ovalle | 1 | Villanueva | ||
| 11-abr-1999 | Sausalito | Everton | 2 | Pereyra (2) | 
| Wanderers | 1 | Navia | ||
| 11-abr-1999 | Maipú | Magallanes | 3 | R. Olivares (2), C. Olivares | 
| Arica | 0 | |||
| 8º Fecha | ||||
| 18-abr-1999 | San Felipe | San Felipe | 0 | |
| Melipilla | 1 | Fernández | ||
| 18-abr-1999 | Antofagasta | Antofagasta | 2 | Zamora, Arancibia | 
| Everton | 2 | Guglielmotti, Arancibia | ||
| 18-abr-1999 | Playa Ancha | Wanderers | 4 | Rojas, J. Pérez, Naif, Neveu | 
| Arica | 0 | |||
| 18-abr-1999 | Maipú | Magallanes | 2 | C. Olivares, Tagle | 
| Ovalle | 0 | |||
| 9º Fecha | ||||
| 24-abr-1999 | Ovalle | Ovalle | 0 | |
| Wanderers | 1 | A. González (P) | ||
| 25-abr-1999 | Melipilla | Melipilla | 2 | Fernández (2) | 
| Magallanes | 2 | C. Olivares (P), Aguilera | ||
| 25-abr-1999 | Antofagasta | Antofagasta | 2 | Correa (A), Erazo | 
| San Felipe | 1 | Rubio | ||
| 25-abr-1999 | Sausalito | Everton | 1 | Arancibia | 
| Arica | 1 | Tello | ||
| 10º Fecha | ||||
| 2-may-1999 | Arica | Arica | 1 | Tello | 
| Ovalle | 1 | Cortés | ||
| 2-may-1999 | Maipú | Magallanes | 3 | C. Olivares (2, 1P), Aguilera | 
| Antofagasta | 0 | |||
| 2-may-1999 | Playa Ancha | Wanderers | 1 | Naif | 
| Melipilla | 0 | |||
| 2-may-1999 | San Felipe | San Felipe | 0 | |
| Everton | 0 | |||
| 11º Fecha | ||||
| 9-may-1999 | Melipilla | Melipilla | 3 | Fernández, Cueto, Gutiérrez | 
| Arica | 0 | |||
| 9-may-1999 | Antofagasta | Antofagasta | 1 | Molina (P) | 
| Wanderers | 3 | Villarroel, A. González (2) | ||
| 9-may-1999 | San Felipe | San Felipe | 1 | González | 
| Magallanes | 1 | Aguilera | ||
| 9-may-1999 | Sausalito | Everton | 1 | Amaya | 
| Ovalle | 2 | Cortés, Gamboa | ||
| 12º Fecha | ||||
| 15-may-1999 | Ovalle | Ovalle | 0 | |
| Melipilla | 1 | Fernández | ||
| 15-may-1999 | Arica | Arica | 2 | Tello (P), Bravo | 
| Antofagasta | 1 | Jirón | ||
| 16-may-1999 | Maipú | Magallanes | 1 | R. Olivares | 
| Everton | 2 | Amaya (2) | ||
| 16-may-1999 | Playa Ancha | Wanderers | 0 | |
| San Felipe | 0 | |||
| 13º Fecha | ||||
| 23-may-1999 | Sausalito | Everton | 1 | Arancibia | 
| Melipilla | 0 | |||
| 23-may-1999 | San Felipe | San Felipe | 1 | Durán | 
| Arica | 0 | |||
| 23-may-1999 | Maipú | Magallanes | 2 | C. Olivares, Fredes | 
| Wanderers | 1 | Santelices | ||
| 23-may-1999 | Antofagasta | Antofagasta | 0 | |
| Ovalle | 0 | |||
| 14º Fecha | ||||
| 29-may-1999 | Ovalle | Ovalle | 1 | Vergnano | 
| San Felipe | 0 | |||
| 29-may-1999 | Arica | Arica | 2 | Fre (2, 1P) | 
| Magallanes | 1 | Correa | ||
| 30-may-1999 | Melipilla | Melipilla | 3 | Cueto, Fernández, Gutiérrez | 
| Antofagasta | 1 | Salas | ||
| 30-may-1999 | Playa Ancha | Wanderers | 0 | |
| Everton | 1 | Amaya | ||
| Zona Sur | ||||
| 1º Fecha | ||||
| 26-feb-1999 | Santa Laura | Unión Española | 2 | Bustos, Acuña | 
| Fernández Vial | 0 | |||
| 27-feb-1999 | San Fernando | Colchagua | 2 | Campos, Muñoz | 
| Linares | 0 | |||
| 28-feb-1999 | Parque Schott | Osorno | 4 | Cataldo, Giganti (P), Barahona, Olea | 
| Ñublense | 5 | Aravena, Cerón, Verdugo, Lizama, Jéldrez | ||
| 2º Fecha | ||||
| 5-mar-1999 | Santa Laura | Unión Española | 0 | |
| U. de Concepción | 1 | Malbrán | ||
| 7-mar-1999 | Concepción | Fernández Vial | 0 | |
| Colchagua | 1 | Salazar | ||
| 7-mar-1999 | Linares | Linares | 1 | Esparza | 
| Osorno | 1 | Cataldo | ||
| 3º Fecha | ||||
| 14-mar-1999 | Concepción | U. de Concepción | 1 | Roldán | 
| de Apoquindo | Ñublense | 1 | Verdugo | |
| 14-mar-1999 | San Fernando | Colchagua | 1 | Brunning | 
| Unión Española | 1 | Gutiérrez | ||
| 14-mar-1999 | Parque Schott | Osorno | 1 | Olea | 
| Fernández Vial | 0 | |||
| 4º Fecha | ||||
| 19-mar-1999 | Santa Laura | Unión Española | 5 | Reyes (2), Junior, J. L. Sánchez, Bustos | 
| Osorno | 3 | Márquez, Giganti, Olea | ||
| 20-mar-1999 | San Fernando | Colchagua | 3 | Castro (P), Brunning, Canales | 
| U. de Concepción | 3 | Gutiérrez, Roldán (2) | ||
| 21-mar-1999 | Linares | Linares | 1 | Carrasco | 
| Ñublense | 0 | |||
| 5º Fecha | ||||
| 28-mar-1999 | Concepción | U. de Concepción | 5 | Rojas, Malbrán, Roldán, Valenzuela, Fernández | 
| Linares | 0 | |||
| 28-mar-1999 | Parque Schott | Osorno | 2 | Barrientos, Olea | 
| Colchagua | 0 | |||
| 28-mar-1999 | Chillán | Ñublense | 1 | Muñoz | 
| Fernández Vial | 1 | Pereira | ||
| 6º Fecha | ||||
| 1-abr-1999 | Santa Laura | Unión Española | 2 | Gutiérrez (2) | 
| Ñublense | 1 | Verdugo | ||
| 4-abr-1999 | Concepción | Fernández Vial | 3 | Carbonell (2), Sanhueza | 
| Linares | 0 | |||
| 4-abr-1999 | Parque Schott | Osorno | 0 | |
| U. de Concepción | 0 | |||
| 7º Fecha | ||||
| 10-abr-1999 | Concepción | U. de Concepción | 1 | Rojas | 
| Fernández Vial | 1 | Rebolledo | ||
| 11-abr-1999 | Chillán | Ñublense | 1 | Oliva (A) | 
| Colchagua | 2 | Salazar, Campos | ||
| 11-abr-1999 | Linares | Linares | 1 | Poblete | 
| Unión Española | 3 | Reyes (P), Queraltó, Akselman | ||
| 8º Fecha | ||||
| 18-abr-1999 | Linares | Linares | 0 | |
| Colchagua | 4 | Brunning (2P), Ibarra, Molina | ||
| 18-abr-1999 | Concepción | Fernández Vial | 0 | |
| Unión Española | 0 | |||
| 18-abr-1999 | Chillán | Ñublense | 4 | Soto, Lizama, Suazo, Verdugo | 
| Osorno | 2 | Casanova, Olea | ||
| 9º Fecha | ||||
| 25-abr-1999 | Concepción | U. de Concepción | 3 | Roldán, Castillo (P), Correa | 
| Unión Española | 3 | Gutiérrez, Reyes, Junior | ||
| 25-abr-1999 | Parque Schott | Osorno | 1 | Cataldo | 
| Linares | 1 | Carrasco | ||
| 25-abr-1999 | San Fernando | Colchagua | 0 | |
| Fernández Vial | 0 | |||
| 10º Fecha | ||||
| 30-abr-1999 | Santa Laura | Unión Española | 3 | J. L. Sánchez, Queraltó, Junior | 
| Colchagua | 0 | |||
| 2-may-1999 | Chillán | Ñublense | 2 | Cerón, Lizama (P) | 
| U. de Concepción | 3 | Almendra (3, 2P) | ||
| 2-may-1999 | Concepción | Fernández Vial | 1 | Vergara | 
| Osorno | 2 | Giganti, Barahona | ||
| 11º Fecha | ||||
| 8-may-1999 | Concepción | U. de Concepción | 3 | Roldán (2), Gutiérrez | 
| Colchagua | 1 | Medina | ||
| 9-may-1999 | Parque Schott | Osorno | 2 | Aguilar, Olea | 
| Unión Española | 3 | Queraltó, Reyes, Junior | ||
| 9-may-1999 | Chillán | Ñublense | 1 | Verdugo | 
| Linares | 1 | Mina | ||
| 12º Fecha | ||||
| 16-may-1999 | San Fernando | Colchagua | 2 | Salazar (2) | 
| Osorno | 3 | Millape, Olea, Muñoz | ||
| 16-may-1999 | Concepción | Fernández Vial | 1 | Carbonell | 
| Ñublense | 0 | |||
| 16-may-1999 | Linares | Linares | 3 | Carrasco, Poblete, Rosales (P) | 
| U. de Concepción | 1 | Almendra | ||
| 13º Fecha | ||||
| 23-may-1999 | Chillán | Ñublense | 2 | Verdugo, Lizama | 
| Unión Española | 0 | |||
| 23-may-1999 | Concepción | U. de Concepción | 2 | Castillo, Gajardo | 
| Osorno | 3 | Pérez (A), Olea (2) | ||
| 23-may-1999 | Linares | Linares | 0 | |
| Fernández Vial | 4 | Zanatta (2), Sanhueza, Carbonell | ||
| 14º Fecha | ||||
| 28-may-1999 | Santa Laura | Unión Española | 4 | Gutiérrez (3), Reyes (P) | 
| Linares | 0 | Illesca | ||
| 29-may-1999 | San Fernando | Colchagua | 3 | Salazar (2), Castro | 
| Ñublense | 1 | Santander | ||
| 30-may-1999 | El Morro | Fernández Vial | 4 | Zanatta (3), Toledo | 
| U. de Concepción | 1 | Gajardo | ||
| Fase Final | ||||
| 1º Fecha | ||||
| 2-jun-1999 | Concepción | U. de Concepción | 5 | Almendra (2P), Roldán (2), Gajardo | 
| Colchagua | 1 | Salazar | ||
| 2-jun-1999 | Ovalle | Ovalle | 2 | Jorquera, Salinas | 
| Magallanes | 0 | |||
| 3-jun-1999 | Sausalito | Everton | 1 | Amaya | 
| San Felipe | 0 | |||
| 3-jun-1999 | Arica | Arica | 0 | |
| Antofagasta | 1 | Molina (P) | ||
| 3-jun-1999 | Melipilla | Melipilla | 0 | |
| Wanderers | 0 | |||
| 3-jun-1999 | Chillán | Ñublense | 0 | |
| Osorno | 2 | Olea, Messen | ||
| 3-jun-1999 | Linares | Linares | 2 | Saavedra (2, 1P) | 
| Fernández Vial | 2 | Carbonell, Sanhueza | ||
| 2º Fecha | ||||
| 5-jun-1999 | Santa Laura | Unión Española | 4 | Reyes (3, 1P), Segovia | 
| Ñublense | 0 | |||
| 6-jun-1999 | Concepción | Fernández Vial | 1 | Pereyra | 
| Ovalle | 1 | Salinas (P) | ||
| 6-jun-1999 | Antofagasta | Antofagasta | 2 | Molina, Cabezas | 
| U. de Concepción | 1 | Rojas | ||
| 6-jun-1999 | Maipú | Magallanes | 1 | Aguilera | 
| Melipilla | 1 | Cueto | ||
| 6-jun-1999 | San Fernando | Colchagua | 1 | Salazar | 
| Osorno | 0 | |||
| 6-jun-1999 | Playa Ancha | Wanderers | 0 | |
| Everton | 1 | Riep | ||
| 6-jun-1999 | San Felipe | San Felipe | 1 | Reyes | 
| Arica | 1 | Beltrand | ||
| 3º Fecha | ||||
| 12-jun-1999 | Arica | Arica | 0 | |
| Wanderers | 2 | Díaz, Carvacho | ||
| 13-jun-1999 | Chillán | Ñublense | 2 | Verdugo, González | 
| Colchagua | 2 | Medina, Salazar | ||
| 13-jun-1999 | Concepción | U. de Concepción | 2 | Rojas, Gutiérrez | 
| San Felipe | 0 | |||
| 13-jun-1999 | Sausalito | Everton | 1 | Rojas | 
| Magallanes | 0 | |||
| 13-jun-1999 | Linares | Linares | 1 | Saavedra (P) | 
| Unión Española | 0 | |||
| 13-jun-1999 | Parque Schott | Osorno | 2 | Muñoz (P), Olea | 
| Antofagasta | 1 | Jirón | ||
| 13-jun-1999 | Melipilla | Melipilla | 1 | Cueto | 
| Fernández Vial | 1 | Carbonell | ||
| 4º Fecha | ||||
| 19-jun-1999 | San Felipe | San Felipe | 3 | Ramos, Craviolatti, Sandoval | 
| Osorno | 2 | Olea (2) | ||
| 20-jun-1999 | Linares | Linares | 1 | Marín | 
| Ñublense | 1 | Santander | ||
| 20-jun-1999 | Antofagasta | Antofagasta | 2 | Stremiz, Salas | 
| Colchagua | 0 | |||
| 20-jun-1999 | Playa Ancha | Wanderers | 2 | Gajardo (A), J. Pérez | 
| U. de Concepción | 0 | |||
| 20-jun-1999 | Santa Laura | Unión Española | 2 | J. L. Sánchez, Queraltó | 
| Ovalle | 2 | Cortés, Gamboa | ||
| 20-jun-1999 | Concepción | Fernández Vial | 1 | Aravena | 
| Everton | 1 | Pereyra | ||
| 20-jun-1999 | Maipú | Magallanes | 0 | |
| Arica | 1 | Fre | ||
| 5º Fecha | ||||
| 26-jun-1999 | Ovalle | Ovalle | 2 | Salinas, Cortés | 
| Linares | 1 | |||
| 26-jun-1999 | Arica | Arica | 3 | Fre (2), Candia (O) | 
| Fernández Vial | 1 | |||
| 27-jun-1999 | Parque Schott | Osorno | 2 | Muñoz (P), Giganti | 
| Wanderers | 1 | Vega (P) | ||
| 27-jun-1999 | Melipilla | Melipilla | 4 | Osorio (2), Solís, Celedón | 
| Unión Española | 0 | |||
| 27-jun-1999 | San Fernando | Colchagua | 4 | Castro, Alonso, Salazar, Canales | 
| San Felipe | 1 | Ramos | ||
| 27-jun-1999 | Concepción | U. de Concepción | 3 | Salcedo, Román, Giganti | 
| Magallanes | 0 | |||
| 27-jun-1999 | Chillán | Ñublense | 2 | Jérez (P), Lizama | 
| Antofagasta | 1 | Salas | ||
| 6º Fecha | ||||
| 3-jul-1999 | Ovalle | Ovalle | 1 | Villanueva | 
| Ñublense | 0 | |||
| 4-jul-1999 | Linares | Linares | 2 | Poblete, Marín | 
| Melipilla | 1 | Fernández | ||
| 4-jul-1999 | Santa Laura | Unión Española | 1 | Valenzuela (P) | 
| Everton | 2 | Fracchia, Pereyra | ||
| 4-jul-1999 | Concepción | Fernández Vial | 1 | Salazar | 
| U. de Concepción | 0 | |||
| 4-jul-1999 | Maipú | Magallanes | 1 | Abrigó | 
| Osorno | 0 | |||
| 4-jul-1999 | Playa Ancha | Wanderers | 2 | Vega, Díaz | 
| Colchagua | 1 | Salazar (P) | ||
| 4-jul-1999 | San Felipe | San Felipe | 2 | Rodríguez (P), Guajardo | 
| Antofagasta | 2 | Zamora, Jirón | ||
| 7º Fecha | ||||
| 10-jul-1999 | Arica | Arica | 1 | Ramírez | 
| Unión Española | 1 | Gutiérrez | ||
| 11-jul-1999 | Chillán | Ñublense | 0 | |
| San Felipe | 2 | Guajardo, Sandoval | ||
| 11-jul-1999 | Sausalito | Everton | 1 | Carreño | 
| Linares | 0 | |||
| 11-jul-1999 | San Fernando | Colchagua | 2 | Molina, Salazar (P) | 
| Magallanes | 3 | Tagle, Torres (2) | ||
| 11-jul-1999 | Antofagasta | Antofagasta | 1 | Jirón | 
| Wanderers | 1 | Neveu | ||
| 11-jul-1999 | Melipilla | Melipilla | 3 | Romero (2), Armijo | 
| Ovalle | 0 | |||
| 11-jul-1999 | Parque Schott | Osorno | 1 | Díaz | 
| Fernández Vial | 1 | Zanatta | ||
| 8º Fecha | ||||
| 17-jul-1999 | Ovalle | Ovalle | 3 | Aliaga, Salinas (P), Cortés | 
| Everton | 1 | Guglielmotti | ||
| 18-jul-1999 | Linares | Linares | 0 | |
| Arica | 0 | |||
| 18-jul-1999 | Maipú | Magallanes | 1 | López | 
| Antofagasta | 1 | Salas | ||
| 18-jul-1999 | Concepción | Fernández Vial | 1 | Aravena | 
| Colchagua | 0 | |||
| 18-jul-1999 | Santa Laura | Unión Española | 2 | Queraltó, Valenzuela (P) | 
| U. de Concepción | 0 | |||
| 18-jul-1999 | Playa Ancha | Wanderers | 3 | Neveu, Naif, A. González | 
| San Felipe | 0 | |||
| 18-jul-1999 | Melipilla | Melipilla | 2 | Osorio (2) | 
| Ñublense | 1 | Cerón | ||
| 9º Fecha | ||||
| 24-jul-1999 | Arica | Arica | 2 | Fernández, Tello | 
| Ovalle | 0 | |||
| 25-jul-1999 | Chillán | Ñublense | 1 | Verdugo | 
| Wanderers | 0 | |||
| 25-jul-1999 | Concepción | U. de Concepción | 1 | Guajardo (P) | 
| Linares | 1 | Mina | ||
| 25-jul-1999 | Antofagasta | Antofagasta | 1 | Reyes | 
| Fernández Vial | 0 | |||
| 25-jul-1999 | Parque Schott | Osorno | 3 | Muñoz (P), Olea, Soto (P) | 
| Unión Española | 2 | Valenzuela (P), Queraltó | ||
| 25-jul-1999 | San Felipe | San Felipe | 1 | Ramos | 
| Magallanes | 3 | Viveros, Aguilera, Torres | ||
| 25-jul-1999 | Sausalito | Everton | 1 | Pereyra | 
| Melipilla | 0 | |||
| 10º Fecha | ||||
| 31-jul-1999 | Santa Laura | Unión Española | 2 | Queraltó, Reinoso | 
| Colchagua | 1 | Salazar | ||
| 31-jul-1999 | Ovalle | Ovalle | 1 | Aliaga | 
| U. de Concepción | 1 | Quiñelén | ||
| 1-ago-1999 | Maipú | Magallanes | 0 | |
| Wanderers | 1 | Vega (P) | ||
| 1-ago-1999 | Linares | Linares | 2 | Marín, Carrasco | 
| Osorno | 3 | Muñoz (P), Millape, Soto (P) | ||
| 1-ago-1999 | Concepción | Fernández Vial | 2 | Zanatta, Aravena | 
| San Felipe | 1 | Ramos | ||
| 1-ago-1999 | Melipilla | Melipilla | 3 | Cueto (P), Osorio, Celedón | 
| Arica | 2 | Lillo, Candia (P) | ||
| 1-ago-1999 | Sausalito | Everton | 1 | Carreño | 
| Ñublense | 0 | |||
| 11º Fecha | ||||
| 7-ago-1999 | Arica | Arica | 1 | Fernández | 
| Everton | 1 | Pereyra | ||
| 7-ago-1999 | Concepción | U. de Concepción | 1 | Quiñelén | 
| Melipilla | 1 | Celedón | ||
| 8-ago-1999 | San Fernando | Colchagua | 3 | Salazar (2), Canales | 
| Linares | 1 | Villalba | ||
| 8-ago-1999 | Chillán | Ñublense | 4 | Jérez (2), Verdugo, Rodríguez | 
| Magallanes | 0 | |||
| 8-ago-1999 | Parque Schott | Osorno | 1 | Olea | 
| Ovalle | 0 | |||
| 8-ago-1999 | Antofagasta | Antofagasta | 1 | Reyes | 
| Unión Española | 2 | Queraltó, Gutiérrez | ||
| 8-ago-1999 | Playa Ancha | Wanderers | 4 | Guerrero, Vega, Robles, Carvacho | 
| Fernández Vial | 0 | |||
| 12º Fecha | ||||
| 14-ago-1999 | Santa Laura | Unión Española | 2 | Reyes, Cerino | 
| San Felipe | 1 | López | ||
| 14-ago-1999 | Ovalle | Ovalle | 4 | Gómez, Cortés (2), Salinas | 
| Colchagua | 1 | Muñoz | ||
| 14-ago-1999 | Arica | Arica | 1 | Fernández | 
| Ñublense | 0 | |||
| 15-ago-1999 | Melipilla | Melipilla | 1 | Cueto | 
| Osorno | 0 | |||
| 15-ago-1999 | Linares | Linares | 5 | Villalba (2), Marín, Carrasco (2) | 
| Antofagasta | 1 | Pino | ||
| 15-ago-1999 | Concepción | Fernández Vial | 2 | Zanatta (2) | 
| Magallanes | 1 | Rivas | ||
| 15-ago-1999 | Sausalito | Everton | 1 | Pereyra | 
| U. de Concepción | 0 | |||
| 13º Fecha | ||||
| 22-ago-1999 | Playa Ancha | Wanderers | 1 | Vega (P) | 
| Unión Española | 1 | Reinoso | ||
| 22-ago-1999 | San Felipe | San Felipe | 2 | Rodríguez, Vergara (A) | 
| Linares | 3 | Villalba (2), Carrasco | ||
| 22-ago-1999 | Concepción | U. de Concepción | 5 | Roldán, Almendra (2), Fernández, Díaz | 
| Arica | 2 | Ramírez, Tello | ||
| 22-ago-1999 | San Fernando | Colchagua | 1 | Medina | 
| Melipilla | 0 | |||
| 22-ago-1999 | Parque Schott | Osorno | 2 | Aguilar, Cataldo | 
| Everton | 0 | |||
| 22-ago-1999 | Antofagasta | Antofagasta | 1 | Reyes | 
| Ovalle | 0 | |||
| 22-ago-1999 | Chillán | Ñublense | 1 | Verdugo | 
| Fernández Vial | 1 | Pereira | ||
| 14º Fecha | ||||
| 28-ago-1999 | Santa Laura | Unión Española | 2 | Roco, Gutiérrez | 
| Magallanes | 1 | R. Olivares | ||
| 28-ago-1999 | Arica | Arica | 3 | Lillo, Rolón, Ramírez | 
| Osorno | 2 | Casanova, Olea | ||
| 28-ago-1999 | Ovalle | Ovalle | 1 | Gómez | 
| San Felipe | 0 | |||
| 29-ago-1999 | Linares | Linares | 1 | Villalba | 
| Wanderers | 1 | Vega (P) | ||
| 29-ago-1999 | Melipilla | Melipilla | 0 | |
| Antofagasta | 1 | Reyes | ||
| 29-ago-1999 | Concepción | U. de Concepción | 1 | Almendra | 
| Ñublense | 2 | Verdugo, Santander | ||
| 29-ago-1999 | Sausalito | Everton | 3 | Carreño, Pereyra, Guhlielmotti | 
| Colchagua | 0 | |||
| 15º Fecha | ||||
| 5-sep-1999 | San Felipe | San Felipe | 0 | |
| Melipilla | 0 | |||
| 5-sep-1999 | Concepción | Fernández Vial | 0 | |
| Unión Española | 3 | Cerino, Reinoso, Queraltó | ||
| 5-sep-1999 | Antofagasta | Antofagasta | 1 | Reyes | 
| Everton | 0 | |||
| 5-sep-1999 | San Fernando | Colchagua | 0 | |
| Arica | 2 | Ramírez, Rolón | ||
| 5-sep-1999 | Maipú | Magallanes | 2 | Tagle, Torres | 
| Linares | 1 | Poblete | ||
| 5-sep-1999 | Parque Schott | Osorno | 2 | Olea (2) | 
| U. de Concepción | 1 | Roldán | ||
| 21-sep-1999 | Playa Ancha | Wanderers | 2 | Vega (P), R. Pérez | 
| Ovalle | 1 | Cortés | ||
| 16º Fecha | ||||
| 12-sep-1999 | Antofagasta | Antofagasta | 0 | |
| Arica | 0 | |||
| 12-sep-1999 | Concepción | Fernández Vial | 4 | Pereira, Aravena (2), Contreras | 
| Linares | 0 | |||
| 12-sep-1999 | Parque Schott | Osorno | 2 | Olea, Giganti | 
| Ñublense | 3 | Jérez (2), Verdugo | ||
| 12-sep-1999 | Playa Ancha | Wanderers | 2 | J. Pérez, R. Pérez | 
| Melipilla | 2 | Celedón (2) | ||
| 29-sep-1999 | San Fernando | Colchagua | 0 | |
| U. de Concepción | 2 | Rojas, Roldán | ||
| 12-oct-1999 | Maipú | Magallanes | 1 | |
| Ovalle | 1 | |||
| 12-oct-1999 | San Felipe | San Felipe | 1 | |
| Everton | 0 | |||
| 17º Fecha | ||||
| 17-sep-1999 | Ovalle | Ovalle | 2 | Salinas, Cortés | 
| Fernández Vial | 0 | |||
| 17-sep-1999 | Arica | Arica | 2 | Muñoz, Bravo | 
| San Felipe | 0 | |||
| 17-sep-1999 | Parque Schott | Osorno | 2 | Olea, Giganti | 
| Colchagua | 2 | Brunning (2) | ||
| 18-sep-1999 | Sausalito | Everton | 1 | Fracchia | 
| Wanderers | 4 | Cabello, R. Pérez, Vega (2) | ||
| 18-sep-1999 | Chillán | Ñublense | 0 | |
| Unión Española | 4 | Queraltó (2), Tapia, C. Sánchez | ||
| 19-sep-1999 | Concepción | U. de Concepción | 2 | Roldán (2) | 
| Antofagasta | 1 | Reyes | ||
| 19-sep-1999 | Melipilla | Melipilla | 5 | Flores (3), Celedón, Osorio | 
| Magallanes | 0 | |||
| 18º Fecha | ||||
| 25-sep-1999 | Concepción | Fernández Vial | 1 | Pereira | 
| Melipilla | 1 | Fernández | ||
| 25-sep-1999 | San Fernando | Colchagua | 1 | Molina | 
| Ñublense | 1 | Roasenda | ||
| 25-sep-1999 | Santa Laura | Unión Española | 3 | Queraltó (2), J. L. Sánchez | 
| Linares | 0 | |||
| 26-sep-1999 | Playa Ancha | Wanderers | 0 | |
| Arica | 2 | Muñoz, Ramírez | ||
| 26-sep-1999 | Maipú | Magallanes | 1 | R. Olivares | 
| Everton | 2 | Acevedo, Amaya (P) | ||
| 26-sep-1999 | Antofagasta | Antofagasta | 1 | Reyes | 
| Osorno | 1 | Olea | ||
| 26-sep-1999 | San Felipe | San Felipe | 1 | Galleguillos | 
| U. de Concepción | 1 | Roldán | ||
| 19º Fecha | ||||
| 2-oct-1999 | Ovalle | Ovalle | 0 | |
| Unión Española | 1 | Gutiérrez | ||
| 2-oct-1999 | San Fernando | Colchagua | 0 | |
| Antofagasta | 2 | Stremis, Cubillos | ||
| 2-oct-1999 | Arica | Arica | 2 | Fernández, Tello | 
| Magallanes | 0 | |||
| 3-oct-1999 | Parque Schott | Osorno | 2 | Díaz, Muñoz | 
| San Felipe | 0 | |||
| 3-oct-1999 | Sausalito | Everton | 0 | |
| Fernández Vial | 0 | |||
| 3-oct-1999 | Coronel | U. de Concepción | 1 | Roldán | 
| Wanderers | 4 | Villarroel, Guerrero, González (2) | ||
| 3-oct-1999 | Chillán | Ñublense | 1 | Verdugo | 
| Linares | 0 | |||
| 20º Fecha | ||||
| 9-oct-1999 | San Felipe | San Felipe | 1 | Fuentes | 
| Colchagua | 0 | |||
| 9-oct-1999 | Santa Laura | Unión Española | 1 | Gutiérrez | 
| Melipilla | 0 | |||
| 10-oct-1999 | Maipú | Magallanes | 4 | Fredes, R. Olivares, Torres, Rivas | 
| U. de Concepción | 1 | Salcedo | ||
| 10-oct-1999 | Playa Ancha | Wanderers | 2 | Vega, R. Pérez | 
| Osorno | 0 | |||
| 10-oct-1999 | El Morro | Fernández Vial | 2 | Zanatta, Carbonell | 
| Arica | 1 | Muñoz | ||
| 10-oct-1999 | Linares | Linares | 3 | Poblete, Carrasco (2) | 
| Ovalle | 4 | Bruna, Cortés, Salinas (2) | ||
| 10-oct-1999 | Antofagasta | Antofagasta | 2 | Cussó, Reyes | 
| Ñublense | 1 | Castro | ||
| 21º Fecha | ||||
| 16-oct-1999 | San Fernando | Colchagua | 1 | Salazar | 
| Wanderers | 2 | R. Pérez, Vega | ||
| 17-oct-1999 | Chillán | Ñublense | 2 | Verdugo, Jérez | 
| Ovalle | 1 | Vergnano | ||
| 17-oct-1999 | Parque Schott | Osorno | 1 | Olea | 
| Magallanes | 0 | |||
| 17-oct-1999 | Melipilla | Melipilla | 1 | Celedón | 
| Linares | 1 | Villalba | ||
| 17-oct-1999 | Concepción | U. de Concepción | 1 | Rojas | 
| Fernández Vial | 0 | |||
| 17-oct-1999 | Sausalito | Everton | 1 | Carreño | 
| Unión Española | 1 | Tapia | ||
| 17-oct-1999 | Antofagasta | Antofagasta | 1 | Jirón | 
| San Felipe | 1 | Durán | ||
| 22º Fecha | ||||
| 23-oct-1999 | Santa Laura | Unión Española | 4 | Queraltó (3), Cáceres | 
| Arica | 1 | Ramírez | ||
| 23-oct-1999 | Linares | Linares | 1 | Villalba | 
| Everton | 0 | |||
| 23-oct-1999 | Ovalle | Ovalle | 2 | Cosmelli, Gamboa | 
| Melipilla | 1 | Romero | ||
| 24-oct-1999 | Playa Ancha | Wanderers | 2 | Vega, Robles | 
| Antofagasta | 1 | Cubillos | ||
| 24-oct-1999 | San Felipe | San Felipe | 3 | Rodríguez, González, Correa | 
| Ñublense | 1 | Lizama | ||
| 24-oct-1999 | Maipú | Magallanes | 0 | |
| Colchagua | 0 | |||
| 24-oct-1999 | Concepción | Fernández Vial | 0 | |
| Osorno | 0 | |||
| 23º Fecha | ||||
| 30-oct-1999 | Sausalito | Everton | 1 | Salinas | 
| Ovalle | 1 | Jorquera | ||
| 30-oct-1999 | San Fernando | Colchagua | 1 | Salazar | 
| Fernández Vial | 2 | Aravena (2) | ||
| 30-oct-1999 | Chillán | Ñublense | 1 | Lizama | 
| Melipilla | 4 | Núñez (A), Caro (2A), Armijo | ||
| 30-oct-1999 | Arica | Arica | 1 | Rolón | 
| Linares | 0 | |||
| 31-oct-1999 | San Felipe | San Felipe | 2 | Durán, Ramos | 
| Wanderers | 2 | Vega, R. Pérez | ||
| 31-oct-1999 | Antofagasta | Antofagasta | 2 | Manríquez, Reyes | 
| Magallanes | 1 | Cortez | ||
| 31-oct-1999 | Coronel | U. de Concepción | 1 | Gutiérrez | 
| Unión Española | 1 | Reinoso | ||
| 24º Fecha | ||||
| 6-nov-1999 | Santa Laura | Unión Española | 2 | Queraltó, Gutiérrez | 
| Osorno | 1 | Giganti | ||
| 6-nov-1999 | Ovalle | Ovalle | 4 | Cosmelli, Villanueva, Vergnano (2) | 
| Arica | 0 | |||
| 6-nov-1999 | Linares | Linares | 3 | Villalba, Valenzuela (A), Saavedra | 
| U. de Concepción | 2 | Rojas, Olivares | ||
| 7-nov-1999 | Playa Ancha | Wanderers | 1 | Vega | 
| Ñublense | 0 | |||
| 7-nov-1999 | Maipú | Magallanes | 3 | Hualquipán, Torres (2) | 
| San Felipe | 2 | Ramos, González | ||
| 7-nov-1999 | Melipilla | Melipilla | 1 | Celedón | 
| Everton | 5 | Carreño (2), Riep (2), Pereyra | ||
| 7-nov-1999 | Concepción | Fernández Vial | 2 | Pereira, Sanhueza | 
| Antofagasta | 3 | Molina, Reyes (2) | ||
| 25º Fecha | ||||
| 13-nov-1999 | San Fernando | Colchagua | 0 | |
| Unión Española | 0 | |||
| 13-nov-1999 | Parque Schott | Osorno | 2 | Soto, Figueroa | 
| Linares | 1 | Mina | ||
| 13-nov-1999 | Arica | Arica | 1 | Rolón | 
| Melipilla | 3 | Avilés (A), Fernández, Solís | ||
| 14-nov-1999 | San Felipe | San Felipe | 0 | |
| Fernández Vial | 0 | |||
| 14-nov-1999 | Playa Ancha | Wanderers | 4 | R. González, Vega (2, 1P), A. González | 
| Magallanes | 0 | |||
| 14-nov-1999 | Chillán | Ñublense | 0 | |
| Everton | 3 | Riep, Pereyra, Carreño | ||
| 14-nov-1999 | Coronel | U. de Concepción | 2 | M. Quiñelén, A. Quiñelén | 
| Ovalle | 0 | |||
| 26º Fecha | ||||
| 20-nov-1999 | Sausalito | Everton | 4 | Carreño, Pereyra, Riep (2) | 
| Arica | 2 | Muñoz, Bravo | ||
| 20-nov-1999 | Ovalle | Ovalle | 1 | Gamboa | 
| Osorno | 2 | Díaz, Muñoz | ||
| 20-nov-1999 | Linares | Linares | 3 | Villalba, Carrasco (2) | 
| Colchagua | 0 | |||
| 20-nov-1999 | Melipilla | Melipilla | 4 | Fernández (2), Flores, Arenas | 
| U. de Concepción | 2 | Castillo, Díaz | ||
| 21-nov-1999 | Concepción | Fernández Vial | 0 | |
| Wanderers | 1 | Vega | ||
| 21-nov-1999 | Santa Laura | Unión Española | 2 | Gutiérrez (2) | 
| Antofagasta | 0 | |||
| 21-nov-1999 | Maipú | Magallanes | 4 | Rivas, Cortés, Torres, Abrigo | 
| Ñublense | 1 | Lizama | ||
| 27º Fecha | ||||
| 27-nov-1999 | San Fernando | Colchagua | 0 | |
| Ovalle | 3 | Villanueva, Gamboa, Cortés | ||
| 27-nov-1999 | San Felipe | San Felipe | 2 | Rodríguez, Ramos | 
| Unión Española | 6 | Reinoso, Gutiérrez, Queraltó (2), Reyes (2) | ||
| 27-nov-1999 | Antofagasta | Antofagasta | 1 | Molina | 
| Linares | 1 | Manríquez (A) | ||
| 27-nov-1999 | Chillán | Ñublense | 0 | |
| Arica | 0 | |||
| 28-nov-1999 | Coronel | U. de Concepción | 1 | Almendra | 
| Everton | 2 | Toro (A), Riep | ||
| 28-nov-1999 | Maipú | Magallanes | 2 | Torres, Rivas | 
| Fernández Vial | 1 | Zanatta | ||
| 28-nov-1999 | Parque Schott | Osorno | 2 | Aguilar, Muñoz | 
| Melipilla | 1 | Celedón | ||
| 28º Fecha | ||||
| 3-dic-1999 | Arica | Arica | 1 | Flores | 
| U. de Concepción | 2 | Castillo, Rojas | ||
| 4-dic-1999 | Santa Laura | Unión Española | 1 | Queraltó | 
| Wanderers | 1 | R. Pérez | ||
| 4-dic-1999 | Sausalito | Everton | 3 | Riep (2), Pereyra | 
| Osorno | 2 | Figueroa, Barahona | ||
| 4-dic-1999 | Linares | Linares | 1 | Villalba | 
| San Felipe | 1 | Ramos | ||
| 4-dic-1999 | Ovalle | Ovalle | 4 | Cortés (3), Farías | 
| Antofagasta | 2 | Molina, Salas | ||
| 5-dic-1999 | Concepción | Fernández Vial | 2 | Zanatta, Rosales | 
| Ñublense | 1 | Rodríguez | ||
| 5-dic-1999 | Melipilla | Melipilla | 4 | Celedón (2), Osorio, Fernández | 
| Colchagua | 2 | Alonso, Vega | ||
| 29º Fecha | ||||
| 8-dic-1999 | Maipú | Magallanes | 1 | Fredes | 
| Unión Española | 1 | Gutiérrez | ||
| 8-dic-1999 | San Fernando | Colchagua | 2 | Alonso, Salazar | 
| Everton | 2 | Riep, Amaya | ||
| 8-dic-1999 | Parque Schott | Osorno | 4 | Díaz, Avilés (A), Aguilar, Figueroa | 
| Arica | 0 | |||
| 8-dic-1999 | Chillán | Ñublense | 2 | Jérez, Rodríguez | 
| U. de Concepción | 0 | |||
| 9-dic-1999 | Playa Ancha | Wanderers | 2 | Pérez, Rojas | 
| Linares | 1 | Villalba | ||
| 9-dic-1999 | Antofagasta | Antofagasta | 3 | Pino, Salas, Neira | 
| Melipilla | 0 | |||
| 9-dic-1999 | San Felipe | San Felipe | 1 | Ramos | 
| Ovalle | 1 | Cosmelli | ||
| 30º Fecha | ||||
| 16-dic-1999 | Coronel | U. de Concepción | 3 | Roldán, Almendra (2) | 
| Osorno | 2 | Muñoz, Flores | ||
| 16-dic-1999 | Arica | Arica | 3 | Rolón (2), Robles | 
| Colchagua | 1 | Dos Santos | ||
| 16-dic-1999 | Ovalle | Ovalle | 1 | Cortés | 
| Wanderers | 1 | Navia | ||
| 16-dic-1999 | Sausalito | Everton | 1 | Figueroa | 
| Antofagasta | 0 | |||
| 16-dic-1999 | Melipilla | Melipilla | 1 | Osorio | 
| San Felipe | 2 | Ramos, Durán | ||
| 16-dic-1999 | Santa Laura | Unión Española | 5 | Fuentes, Gutiérrez (3), Queraltó | 
| Fernández Vial | 0 | |||
| 16-dic-1999 | Linares | Linares | 0 | |
| Magallanes | 0 | |||