| 1. Round | 16/08/2020 | NK Osijek II | - | HNK Orijent Rijeka | 0:0 | ||||
| 2. Round | 21/08/2020 | Hrvatski Dragovoljac | - | NK Osijek II | 2:1 | ||||
| 4. Round | 13/09/2020 | NK Osijek II | - | NK Junak Sinj | 2:0 | ||||
| 5. Round | 16/09/2020 | NK Dugopolje | - | NK Osijek II | 0:1 | ||||
| 6. Round | 20/09/2020 | NK Osijek II | - | NK Međimurje | 6:0 |  |
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| 3. Round | 23/09/2020 | NK Osijek II | - | NK Croatia Zmijavci | 0:1 | ||||
| 7. Round | 26/09/2020 | NK Inter Zaprešić | - | NK Osijek II | 0:1 | ||||
| 8. Round | 30/09/2020 | NK Osijek II | - | NK Kustošija | 1:0 | ||||
| 9. Round | 03/10/2020 | NK Opatija | - | NK Osijek II | 1:1 | ||||
| 10. Round | 19/10/2020 | NK Osijek II | - | Dinamo Zagreb II | 1:1 | ||||
| 11. Round | 25/10/2020 | NK BSK Bijelo Brdo | - | NK Osijek II | 0:0 | ||||
| 12. Round | 31/10/2020 | NK Osijek II | - | Hajduk Split II | 1:1 | ||||
| 13. Round | 06/11/2020 | NK Sesvete | - | NK Osijek II | 1:5 |  |
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| 14. Round | 22/11/2020 | NK Osijek II | - | NK Solin | 2:0 | ||||
| 15. Round | 30/11/2020 | NK Rudeš | - | NK Osijek II | 1:0 | ||||
| 16. Round | 06/12/2020 | NK Osijek II | - | HNK Cibalia | 0:0 | ||||
| 17. Round | 12/12/2020 | NK Dubrava | - | NK Osijek II | 2:1 |
North Macedonia