| 19. Jornada | 20.12.2008 | AS Livorno | - | Sassuolo | 3:2 | ||||
| 24. Jornada | 07.02.2009 | AS Livorno | - | Piacenza Calcio | 3:0 | ||||
| 26. Jornada | 17.02.2009 | AS Livorno | - | AS Bari | 1:1 | ||||
| 27. Jornada | 21.02.2009 | US Grosseto FC | - | AS Livorno | 2:3 | ||||
| 31. Jornada | 17.03.2009 | Rimini Calcio | - | AS Livorno | 1:1 | ||||
| 33. Jornada | 29.03.2009 | Brescia Calcio | - | AS Livorno | 2:2 | ||||
| 34. Jornada | 04.04.2009 | AS Livorno | - | Vicenza Calcio | 1:1 | ||||
| 36. Jornada | 18.04.2009 | AS Livorno | - | Parma FC | 2:2 |  |
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| 35. Jornada | 21.04.2009 | Treviso FBC | - | AS Livorno | 0:4 |  |
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| 37. Jornada | 25.04.2009 | AS Livorno | - | Modena FC | 1:2 | ||||
| 38. Jornada | 02.05.2009 | US Salernitana 1919 | - | AS Livorno | 0:2 | ||||
| 42. Jornada | 30.05.2009 | Ascoli Calcio | - | AS Livorno | 2:3 |
Italia