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| H (Match allé) | Empoli FC | - | Brescia Calcio | 1:1 (1:1) | ||
| R (match retour) | Brescia Calcio | - | Empoli FC | 3:0 (0:0) | ||
| H (Match allé): 07.06.2009 19:00 | R (match retour): 11.06.2009 21:00 | vainqueur: Brescia Calcio | ||||
| H (Match allé) | US Grosseto FC | - | AS Livorno | 2:0 (0:0) | ||
| R (match retour) | AS Livorno | - | US Grosseto FC | 4:1 (2:1) | ||
| H (Match allé): 07.06.2009 21:00 | R (match retour): 11.06.2009 19:00 | vainqueur: AS Livorno | ||||
