| 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 |
| 2008-10-25 | BarivGrossetoSerie B · Italy | 3–1 | Serie B · Italy |
| 2008-10-18 | GrossetovSalernitanaSerie B · Italy | 6–2 | Serie B · Italy |
| 2008-10-12 | AscolivGrossetoSerie B · Italy | 0–2 | Serie B · Italy |
| 2008-10-04 | GrossetovAlbinoleffeSerie B · Italy | 2–2 | Serie B · Italy |
| 2008-09-27 | LivornovGrossetoSerie B · Italy | 0–0 | Serie B · Italy |
| 2008-09-23 | AvellinovGrossetoSerie B · Italy | 2–2 | Serie B · Italy |
| 2008-09-20 | GrossetovParmaSerie B · Italy | 1–0 | Serie B · Italy |
| 2008-09-13 | SassuolovGrossetoSerie B · Italy | 4–0 | Serie B · Italy |
| 2008-09-07 | GrossetovPiacenzaSerie B · Italy | 3–0 | Serie B · Italy |
| 2008-08-30 | PisavGrossetoSerie B · Italy | 1–2 | Serie B · Italy |
| 2008-06-01 | SpeziavGrossetoSerie B · Italy | 2–2 | Serie B · Italy |
| 2008-05-25 | GrossetovChievoSerie B · Italy | 1–1 | Serie B · Italy |
| 2008-05-17 | PiacenzavGrossetoSerie B · Italy | 1–1 | Serie B · Italy |
| 2008-05-14 | TrevisovGrossetoSerie B · Italy | 2–1 | Serie B · Italy |
| 2008-05-10 | GrossetovBolognaSerie B · Italy | 3–0 | Serie B · Italy |
| 2008-04-26 | GrossetovFrosinoneSerie B · Italy | 1–1 | Serie B · Italy |
| 2008-04-19 | AscolivGrossetoSerie B · Italy | 3–5 | Serie B · Italy |
| 2008-04-12 | GrossetovTriestinaSerie B · Italy | 1–2 | Serie B · Italy |
| 2008-04-05 | AvellinovGrossetoSerie B · Italy | 0–3 | Serie B · Italy |
| 2008-03-29 | GrossetovLecceSerie B · Italy | 1–1 | Serie B · Italy |
| 2008-03-21 | PisavGrossetoSerie B · Italy | 0–0 | Serie B · Italy |
| 2008-03-18 | GrossetovMantovaSerie B · Italy | 1–0 | Serie B · Italy |
| 2008-03-15 | MessinavGrossetoSerie B · Italy | 1–1 | Serie B · Italy |
| 2008-03-08 | GrossetovBariSerie B · Italy | 2–2 | Serie B · Italy |
| 2008-03-01 | VicenzavGrossetoSerie B · Italy | 0–0 | Serie B · Italy |
| 2008-02-23 | GrossetovRavennaSerie B · Italy | 2–2 | Serie B · Italy |
| 2008-02-16 | RiminivGrossetoSerie B · Italy | 2–0 | Serie B · Italy |
| 2008-02-12 | CesenavGrossetoSerie B · Italy | 0–0 | Serie B · Italy |
| 2008-02-09 | GrossetovAlbinoleffeSerie B · Italy | 2–2 | Serie B · Italy |
| 2008-02-02 | BresciavGrossetoSerie B · Italy | 4–1 | Serie B · Italy |
| 2008-01-26 | GrossetovModenaSerie B · Italy | 0–2 | Serie B · Italy |
| 2008-01-19 | GrossetovSpeziaSerie B · Italy | 3–0 | Serie B · Italy |
| 2008-01-12 | ChievovGrossetoSerie B · Italy | 2–0 | Serie B · Italy |