| 1. Round | 30/08/2008 | Pisa Calcio | - | US Grosseto FC | 1:2 | ||||
| 2. Round | 07/09/2008 | US Grosseto FC | - | Piacenza Calcio | 3:0 | ||||
| 3. Round | 13/09/2008 | Sassuolo Calcio | - | US Grosseto FC | 4:0 |  |
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| 5. Round | 23/09/2008 | US Avellino | - | US Grosseto FC | 2:2 | ||||
| 6. Round | 27/09/2008 | AS Livorno | - | US Grosseto FC | 0:0 | ||||
| 7. Round | 04/10/2008 | US Grosseto FC | - | UC AlbinoLeffe | 2:2 | ||||
| 8. Round | 12/10/2008 | Ascoli Calcio | - | US Grosseto FC | 0:2 |  |
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| 9. Round | 18/10/2008 | US Grosseto FC | - | US Salernitana 1919 | 6:2 | |
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| 10. Round | 25/10/2008 | AS Bari | - | US Grosseto FC | 3:1 | ||||
| 11. Round | 28/10/2008 | US Grosseto FC | - | Treviso FBC | 4:1 | ||||
| 12. Round | 01/11/2008 | AC Mantova | - | US Grosseto FC | 2:1 | ||||
| 13. Round | 08/11/2008 | US Grosseto FC | - | Modena FC | 2:1 | ||||
| 14. Round | 17/11/2008 | Empoli FC | - | US Grosseto FC | 1:1 | ||||
| 15. Round | 22/11/2008 | US Grosseto FC | - | US Triestina | 1:0 | ||||
| 16. Round | 29/11/2008 | Vicenza Calcio | - | US Grosseto FC | 5:0 |
Italy