Head to Head
| Italy Serie D | 2024/03/10 14:00 | Poggibonsi v Grosseto | W | 1-2 |
| Italy Serie D | 2023/11/01 17:00 | Grosseto v Poggibonsi | W | 1-0 |
| Italy Serie D | 2023/01/08 13:30 | Grosseto v Poggibonsi | L | 1-2 |
| Italy Serie D | 2022/09/04 13:00 | Poggibonsi v Grosseto | L | 3-0 |
Home History
| Italy Serie D | 2024/09/15 13:00 | ASD Seravezza Calcio v Grosseto | D | 1-1 |
| Italy Serie D | 2024/09/08 13:00 | Grosseto v Orvietana | W | 3-0 |
| Club Friendly List | 2024/08/19 16:00 | Grosseto v Aquila 1902 Montevarchi | D | 0-0 |
| Europe Friendlies | 2024/08/14 15:00 | Ghiviborgo v Grosseto | D | 4-4 |
| Club Friendly List | 2024/08/07 16:00 | Fiorentina U19 v Grosseto | L | 3-2 |
| Europe Friendlies | 2024/08/05 18:00 | Grosseto v Fiorentina XI | L | 2-7 |
| Club Friendly List | 2024/08/05 18:00 | Grosseto v Fiorentina | L | 2-7 |
| Italy Serie D Play-Offs | 2024/05/19 18:30 | Grosseto v ASD Tau Calcio Altopascio | W | 3-0 |
Away History
| Italy Serie D | 2024/09/15 13:00 | Poggibonsi v Fezzanese | D | 2-2 |
| Italy Serie D | 2024/09/08 13:00 | ASD Sporting Trestina v Poggibonsi | W | 0-1 |
| Club Friendly List | 2024/08/10 14:00 | Pisa U19 v Poggibonsi | L | 2-1 |
| Italy Serie D | 2024/05/05 13:00 | Poggibonsi v Figline | W | 4-1 |
| Italy Serie D | 2024/04/28 13:00 | Sangiovannese v Poggibonsi | L | 2-1 |
| Italy Serie D | 2024/04/21 13:00 | Poggibonsi v SC Cenaia | W | 4-1 |
| Italy Serie D | 2024/04/14 13:00 | ASD Seravezza Calcio v Poggibonsi | W | 1-2 |
| Italy Serie D | 2024/04/07 13:00 | Poggibonsi v Gavorrano | W | 4-1 |