| 3. Jornada | 28.07.2019 | Club Olimpia | - | River Plate | 2:1 | ||||
| 5. Jornada | 11.08.2019 | Club Olimpia | - | Sportivo Luqueño | 3:1 |  |
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| 6. Jornada | 17.08.2019 | Cerro Porteño | - | Club Olimpia | 0:0 | |
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| 7. Jornada | 26.08.2019 | Club Olimpia | - | Deportivo Santaní | 4:0 | ||||
| 10. Jornada | 22.09.2019 | Guaraní | - | Club Olimpia | 1:1 | ||||
| 12. Jornada | 29.09.2019 | Club Olimpia | - | General Díaz | 2:0 | |
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| 13. Jornada | 06.10.2019 | Club Olimpia | - | Club Nacional | 3:0 | ||||
| 14. Jornada | 20.10.2019 | River Plate | - | Club Olimpia | 0:1 | ||||
| 15. Jornada | 27.10.2019 | Club Olimpia | - | Libertad | 2:1 | ||||
| 18. Jornada | 12.11.2019 | Deportivo Santaní | - | Club Olimpia | 0:1 | |
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| 20. Jornada | 02.12.2019 | San Lorenzo | - | Club Olimpia | 1:4 | ||||
| 21. Jornada | 08.12.2019 | Club Olimpia | - | Guaraní | 2:2 | |
Colombia