| 3. Round | 27/07/2019 | Club Olimpia | - | River Plate | 2:1 | ||||
| 5. Round | 11/08/2019 | Club Olimpia | - | Sportivo Luqueño | 3:1 |  |
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| 6. Round | 17/08/2019 | Cerro Porteño | - | Club Olimpia | 0:0 | |
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| 7. Round | 25/08/2019 | Club Olimpia | - | Deportivo Santaní | 4:0 | ||||
| 10. Round | 22/09/2019 | Guaraní | - | Club Olimpia | 1:1 | ||||
| 12. Round | 29/09/2019 | Club Olimpia | - | General Díaz | 2:0 | |
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| 13. Round | 06/10/2019 | Club Olimpia | - | Club Nacional | 3:0 | ||||
| 14. Round | 20/10/2019 | River Plate | - | Club Olimpia | 0:1 | ||||
| 15. Round | 27/10/2019 | Club Olimpia | - | Libertad | 2:1 | ||||
| 18. Round | 11/11/2019 | Deportivo Santaní | - | Club Olimpia | 0:1 | |
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| 20. Round | 01/12/2019 | San Lorenzo | - | Club Olimpia | 1:4 | ||||
| 21. Round | 08/12/2019 | Club Olimpia | - | Guaraní | 2:2 | |
Colombia