| 3. Round | 07/10/2020 | Matelica | - | FC Südtirol | 1:1 | ||||
| 4. Round | 11/10/2020 | Vis Pesaro | - | Matelica | 2:1 | ||||
| 6. Round | 21/10/2020 | Mantova 1911 SSD | - | Matelica | 5:2 | ||||
| 7. Round | 25/10/2020 | Matelica | - | US Arezzo | 2:2 |  |
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| 8. Round | 01/11/2020 | Virtus Verona | - | Matelica | 1:0 | ||||
| 10. Round | 11/11/2020 | FC Legnago Salus | - | Matelica | 1:2 | ||||
| 11. Round | 15/11/2020 | Calcio Padova | - | Matelica | 3:0 | ||||
| 12. Round | 22/11/2020 | Matelica | - | Cesena FC | 2:2 | ||||
| 13. Round | 29/11/2020 | Fermana FC | - | Matelica | 1:1 | ||||
| 14. Round | 05/12/2020 | Matelica | - | AS Gubbio | 1:3 |
Italy