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| 23.09.2008 | 20:30 | AC Ancona | - | Brescia Calcio | 2:0 (1:0) | |
| 20:30 | US Avellino | - | US Grosseto FC | 2:2 (0:1) | ||
| 20:30 | AS Bari | - | AS Livorno | 0:0 (0:0) | ||
| 20:30 | AC Mantova | - | Ascoli Calcio | 0:0 (0:0) | ||
| 20:30 | Parma FC | - | Frosinone Calcio | 2:2 (1:1) | ||
| 20:30 | Piacenza Calcio | - | Rimini Calcio | 0:0 (0:0) | ||
| 20:30 | Pisa Calcio | - | Vicenza Calcio | 0:2 (0:1) | ||
| 20:30 | US Salernitana 1919 | - | US Triestina | 0:1 (0:1) | ||
| 20:30 | Sassuolo Calcio | - | UC AlbinoLeffe | 1:0 (0:0) | ||
| 20:30 | Treviso FBC | - | AS Cittadella | 0:1 (0:1) | ||
| 20:30 | Empoli FC | - | Modena FC | 3:1 (1:1) |
| » Classement | équipe recevante | à l'extérieur | Premier tour | Second tour |
| # | Équipe | M. | G. | N. | P. | Buts | Diff. | Pts. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Sassuolo Calcio | 5 | 3 | 1 | 1 | 9:3 | 6 | 10 |
| 2 |
|
UC AlbinoLeffe | 5 | 3 | 1 | 1 | 5:2 | 3 | 10 |
| 3 |
|
US Grosseto FC | 5 | 3 | 1 | 1 | 8:7 | 1 | 10 |
| 4 |
|
US Salernitana 1919 | 5 | 3 | 1 | 1 | 5:3 | 2 | 10 |
| 5 |
|
AC Mantova | 5 | 2 | 3 | 0 | 5:1 | 4 | 9 |
| 6 |
|
Empoli FC | 5 | 2 | 3 | 0 | 7:4 | 3 | 9 |
|
US Triestina | 5 | 2 | 3 | 0 | 7:4 | 3 | 9 | |
| 8 |
|
Piacenza Calcio | 5 | 2 | 2 | 1 | 3:4 | -1 | 8 |
| 9 |
|
AS Livorno | 5 | 1 | 4 | 0 | 6:4 | 2 | 7 |
| 10 |
|
AS Bari | 5 | 1 | 4 | 0 | 4:3 | 1 | 7 |
| 11 |
|
Brescia Calcio | 5 | 1 | 3 | 1 | 5:6 | -1 | 6 |
| 12 |
|
Parma FC | 5 | 1 | 2 | 2 | 7:6 | 1 | 5 |
| 13 |
|
Vicenza Calcio | 5 | 1 | 2 | 2 | 4:4 | 0 | 5 |
| 14 |
|
Rimini Calcio | 5 | 1 | 2 | 2 | 5:6 | -1 | 5 |
| 15 |
|
AC Ancona | 5 | 1 | 2 | 2 | 5:7 | -2 | 5 |
|
Frosinone Calcio | 5 | 1 | 2 | 2 | 5:7 | -2 | 5 | |
| 17 |
|
AS Cittadella | 5 | 1 | 2 | 2 | 1:3 | -2 | 5 |
| 18 |
|
Ascoli Calcio | 5 | 1 | 3 | 1 | 3:3 | 0 | 4 |
| 19 |
|
Pisa Calcio | 5 | 1 | 1 | 3 | 4:8 | -4 | 4 |
| 20 |
|
Treviso FBC | 5 | 1 | 2 | 2 | 3:4 | -1 | 1 |
| 21 |
|
US Avellino | 5 | 0 | 2 | 3 | 5:10 | -5 | 0 |
| 22 |
|
Modena FC | 5 | 0 | 0 | 5 | 4:11 | -7 | 0 |
