| 2. Round | 05/09/2021 | US Pistoiese | - | US Grosseto FC | 1:1 | ||||
| 3. Round | 11/09/2021 | US Grosseto FC | - | Ancona 1905 | 0:0 | ||||
| 4. Round | 19/09/2021 | Carrarese Calcio | - | US Grosseto FC | 2:1 |  |
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| 5. Round | 25/09/2021 | US Grosseto FC | - | AS Gubbio | 1:1 |  |
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| 6. Round | 28/09/2021 | Fermana FC | - | US Grosseto FC | 2:0 | ||||
| 7. Round | 02/10/2021 | US Grosseto FC | - | Cesena FC | 0:1 | |
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| 8. Round | 10/10/2021 | Viterbese | - | US Grosseto FC | 0:1 | ||||
| 9. Round | 16/10/2021 | US Grosseto FC | - | AC Reggiana 1919 | 0:0 | ||||
| 10. Round | 19/10/2021 | US Grosseto FC | - | SSD Città di Teramo | 1:1 | ||||
| 11. Round | 23/10/2021 | Imolese Calcio | - | US Grosseto FC | 5:0 | |
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| 12. Round | 31/10/2021 | US Grosseto FC | - | Vis Pesaro | 1:1 | ||||
| 13. Round | 06/11/2021 | US Pontedera | - | US Grosseto FC | 2:0 | |
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| 15. Round | 21/11/2021 | US Grosseto FC | - | Aquila Montevarchi | 1:2 | ||||
| 16. Round | 27/11/2021 | ACN Siena 1904 | - | US Grosseto FC | 1:3 | ||||
| 17. Round | 05/12/2021 | US Grosseto FC | - | Delfino Pescara | 1:2 | ||||
| 18. Round | 12/12/2021 | Lucchese | - | US Grosseto FC | 0:0 | |
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| 19. Round | 19/12/2021 | US Grosseto FC | - | Olbia Calcio | 0:1 | ||||
| 20. Round | 22/12/2021 | Modena FC | - | US Grosseto FC | 2:1 |
Bosnia-Herzegovina