 |
 |
|
|
| 1st(1st leg) | San Marcos | - | Deportes Iquique | 0:2 (0:1) | ||
| 2nd (2nd leg) | Deportes Iquique | - | San Marcos | 2:0 (1:0) | ||
| 1st(1st leg): 31/05/2019 02:00 | 2nd (2nd leg): 05/06/2019 20:30 | Winner: Deportes Iquique | ||||
| 1st(1st leg) | Palestino | - | Santiago Morning | 4:3 (1:1) | ||
| 2nd (2nd leg) | Santiago Morning | - | Palestino | 1:1 (0:1) | ||
| 1st(1st leg): 05/06/2019 20:30 | 2nd (2nd leg): 09/06/2019 20:30 | Winner: Palestino | ||||
| 1st(1st leg) | Trasandino de Los Andes | - | Everton | 0:1 (0:0) | ||
| 2nd (2nd leg) | Everton | - | Trasandino de Los Andes | 1:0 (0:0) | ||
| 1st(1st leg): 08/06/2019 20:00 | 2nd (2nd leg): 07/07/2019 00:00 | Winner: Everton | ||||
| 1st(1st leg) | Rangers | - | Universidad de Chile | 0:2 (0:2) | ||
| 2nd (2nd leg) | Universidad de Chile | - | Rangers | 1:1 (0:1) | ||
| 1st(1st leg): 08/06/2019 20:00 | 2nd (2nd leg): 12/06/2019 23:15 | Winner: Universidad de Chile | ||||
| 1st(1st leg) | CD Magallanes | - | Unión La Calera | 0:2 (0:1) | ||
| 2nd (2nd leg) | Unión La Calera | - | CD Magallanes | 3:2 (2:2) | ||
| 1st(1st leg): 08/06/2019 20:30 | 2nd (2nd leg): 13/06/2019 22:30 | Winner: Unión La Calera | ||||
| 1st(1st leg) | Melipilla | - | Unión Española | 0:0 (0:0) | ||
| 2nd (2nd leg) | Unión Española | - | Melipilla | 4:3 (0:0, 0:0) pso | ||
| 1st(1st leg): 08/06/2019 20:30 | 2nd (2nd leg): 11/07/2019 01:00 | Winner: Unión Española | ||||
| 1st(1st leg) | Santiago Wanderers | - | Audax Italiano | 1:2 (1:1) | ||
| 2nd (2nd leg) | Audax Italiano | - | Santiago Wanderers | 3:1 (2:0) | ||
| 1st(1st leg): 08/06/2019 22:30 | 2nd (2nd leg): 11/06/2019 23:00 | Winner: Audax Italiano | ||||
| 1st(1st leg) | Vallenar | - | Cobresal | 1:0 (1:0) | ||
| 2nd (2nd leg) | Cobresal | - | Vallenar | 3:0 (2:0) | ||
| 1st(1st leg): 08/06/2019 23:00 | 2nd (2nd leg): 09/07/2019 20:00 | Winner: Cobresal | ||||
| 1st(1st leg) | Santa Cruz | - | O'Higgins | 3:2 (2:0) | ||
| 2nd (2nd leg) | O'Higgins | - | Santa Cruz | 4:1 (2:0) | ||
| 1st(1st leg): 08/06/2019 23:00 | 2nd (2nd leg): 13/06/2019 00:30 | Winner: O'Higgins | ||||
| 1st(1st leg) | La Serena | - | Universidad Católica | 1:0 (1:0) | ||
| 2nd (2nd leg) | Universidad Católica | - | La Serena | 6:5 (1:0, 2:1) pso | ||
| 1st(1st leg): 09/06/2019 01:00 | 2nd (2nd leg): 10/07/2019 01:00 | Winner: Universidad Católica | ||||
| 1st(1st leg) | Barnechea | - | Antofagasta | 1:2 (0:1) | ||
| 2nd (2nd leg) | Antofagasta | - | Barnechea | 3:4 (1:0, 1:2) pso | ||
| 1st(1st leg): 09/06/2019 17:00 | 2nd (2nd leg): 13/06/2019 21:00 | Winner: Barnechea | ||||
| 1st(1st leg) | Deportes Temuco | - | Huachipato | 2:1 (1:1) | ||
| 2nd (2nd leg) | Huachipato | - | Deportes Temuco | 1:1 (0:0) | ||
| 1st(1st leg): 09/06/2019 17:30 | 2nd (2nd leg): 07/07/2019 17:00 | Winner: Deportes Temuco | ||||
| 1st(1st leg) | Unión San Felipe | - | Coquimbo Unido | 3:1 (3:0) | ||
| 2nd (2nd leg) | Coquimbo Unido | - | Unión San Felipe | 1:1 (0:1) | ||
| 1st(1st leg): 09/06/2019 20:00 | 2nd (2nd leg): 14/06/2019 00:30 | Winner: Unión San Felipe | ||||
| 1st(1st leg) | Puerto Montt | - | Colo-Colo | 2:0 (1:0) | ||
| 2nd (2nd leg) | Colo-Colo | - | Puerto Montt | 5:3 (2:2, 4:2) pso | ||
| 1st(1st leg): 09/06/2019 20:00 | 2nd (2nd leg): 14/06/2019 01:00 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Ñublense | - | Curicó Unido | 0:1 (0:0) | ||
| 2nd (2nd leg) | Curicó Unido | - | Ñublense | 2:4 (1:1, 1:2) pso | ||
| 1st(1st leg): 09/06/2019 20:30 | 2nd (2nd leg): 13/06/2019 00:30 | Winner: Ñublense | ||||
| 1st(1st leg) | Deportes Valdivia | - | Universidad de Concepción | 0:0 (0:0) | ||
| 2nd (2nd leg) | Universidad de Concepción | - | Deportes Valdivia | 3:5 (0:1, 1:1) pso | ||
| 1st(1st leg): 09/06/2019 21:00 | 2nd (2nd leg): 13/06/2019 00:00 | Winner: Deportes Valdivia | ||||
