| 2009-12-12 | PiacenzavGrossetoSerie B · Italy | 0–1 | Serie B · Italy |
| 2009-12-08 | GrossetovAlbinoleffeSerie B · Italy | 2–2 | Serie B · Italy |
| 2009-12-05 | GrossetovAnconaSerie B · Italy | 2–0 | Serie B · Italy |
| 2009-11-28 | LeccevGrossetoSerie B · Italy | 3–2 | Serie B · Italy |
| 2009-11-21 | GrossetovSalernitanaSerie B · Italy | 2–2 | Serie B · Italy |
| 2009-11-07 | VicenzavGrossetoSerie B · Italy | 0–0 | Serie B · Italy |
| 2009-10-31 | GrossetovAscoliSerie B · Italy | 2–1 | Serie B · Italy |
| 2009-10-24 | CesenavGrossetoSerie B · Italy | 2–2 | Serie B · Italy |
| 2009-10-17 | GrossetovPadovaSerie B · Italy | 2–2 | Serie B · Italy |
| 2009-10-11 | SassuolovGrossetoSerie B · Italy | 2–3 | Serie B · Italy |
| 2009-10-03 | MantovavGrossetoSerie B · Italy | 2–0 | Serie B · Italy |
| 2009-09-26 | GrossetovBresciaSerie B · Italy | 2–1 | Serie B · Italy |
| 2009-09-22 | CrotonevGrossetoSerie B · Italy | 0–0 | Serie B · Italy |
| 2009-09-19 | GrossetovModenaSerie B · Italy | 3–1 | Serie B · Italy |
| 2009-09-12 | CittadellavGrossetoSerie B · Italy | 1–1 | Serie B · Italy |
| 2009-09-06 | GrossetovGallipoliSerie B · Italy | 2–2 | Serie B · Italy |
| 2009-08-29 | TriestinavGrossetoSerie B · Italy | 1–0 | Serie B · Italy |
| 2009-08-21 | GrossetovTorinoSerie B · Italy | 0–3 | Serie B · Italy |
| 2009-05-30 | GrossetovFrosinoneSerie B · Italy | 2–1 | Serie B · Italy |
| 2009-05-23 | AnconavGrossetoSerie B · Italy | 1–1 | Serie B · Italy |
| 2009-05-18 | GrossetovBresciaSerie B · Italy | 2–1 | Serie B · Italy |
| 2009-05-09 | RiminivGrossetoSerie B · Italy | 2–0 | Serie B · Italy |
| 2009-05-02 | CittadellavGrossetoSerie B · Italy | 0–2 | Serie B · Italy |
| 2009-04-25 | GrossetovVicenzaSerie B · Italy | 2–1 | Serie B · Italy |
| 2009-04-21 | GrossetovEmpoliSerie B · Italy | 2–2 | Serie B · Italy |
| 2009-04-17 | TriestinavGrossetoSerie B · Italy | 2–3 | Serie B · Italy |
| 2009-04-04 | ModenavGrossetoSerie B · Italy | 1–1 | Serie B · Italy |
| 2009-03-29 | GrossetovMantovaSerie B · Italy | 1–1 | Serie B · Italy |
| 2009-03-23 | TrevisovGrossetoSerie B · Italy | 1–0 | Serie B · Italy |
| 2009-03-17 | GrossetovBariSerie B · Italy | 1–1 | Serie B · Italy |
| 2009-03-14 | SalernitanavGrossetoSerie B · Italy | 2–0 | Serie B · Italy |
| 2009-03-07 | GrossetovAscoliSerie B · Italy | 1–0 | Serie B · Italy |
| 2009-03-02 | AlbinoleffevGrossetoSerie B · Italy | 4–1 | Serie B · Italy |
| 2009-02-21 | GrossetovLivornoSerie B · Italy | 2–3 | Serie B · Italy |
| 2009-02-17 | GrossetovAvellinoSerie B · Italy | 3–2 | Serie B · Italy |
| 2009-02-14 | ParmavGrossetoSerie B · Italy | 4–0 | Serie B · Italy |
| 2009-02-07 | GrossetovSassuoloSerie B · Italy | 1–2 | Serie B · Italy |
| 2009-01-31 | PiacenzavGrossetoSerie B · Italy | 2–3 | Serie B · Italy |
| 2009-01-24 | GrossetovPisaSerie B · Italy | 4–1 | Serie B · Italy |
| 2009-01-19 | FrosinonevGrossetoSerie B · Italy | 2–0 | Serie B · Italy |
| 2009-01-10 | GrossetovAnconaSerie B · Italy | 2–1 | Serie B · Italy |
| 2008-12-19 | BresciavGrossetoSerie B · Italy | 1–0 | Serie B · Italy |
| 2008-12-13 | GrossetovRiminiSerie B · Italy | 1–3 | Serie B · Italy |
| 2008-12-06 | GrossetovCittadellaSerie B · Italy | 1–1 | Serie B · Italy |
| 2008-11-29 | VicenzavGrossetoSerie B · Italy | 5–0 | Serie B · Italy |
| 2008-11-22 | GrossetovTriestinaSerie B · Italy | 1–0 | Serie B · Italy |
| 2008-11-17 | EmpolivGrossetoSerie B · Italy | 1–1 | Serie B · Italy |
| 2008-11-08 | GrossetovModenaSerie B · Italy | 2–1 | Serie B · Italy |
| 2008-11-01 | MantovavGrossetoSerie B · Italy | 2–1 | Serie B · Italy |
| 2008-10-28 | GrossetovTrevisoSerie B · Italy | 4–1 | Serie B · Italy |