| 15. Ronde | 01.11.2008 | Grimsby Town | - | Darlington FC | 1:2 | ||||
| 16. Ronde | 15.11.2008 | Darlington FC | - | Lincoln City | 2:0 |  |
|||
| 17. Ronde | 22.11.2008 | Brentford FC | - | Darlington FC | 1:1 | |
 |
||
| 18. Ronde | 25.11.2008 | Darlington FC | - | Chester City | 1:2 | ||||
| 20. Ronde | 13.12.2008 | Morecambe FC | - | Darlington FC | 1:0 | |
|||
| 21. Ronde | 20.12.2008 | Darlington FC | - | Barnet FC | 2:2 | ||||
| 22. Ronde | 26.12.2008 | Bury FC | - | Darlington FC | 2:2 | |
|||
| 23. Ronde | 28.12.2008 | Darlington FC | - | Chesterfield FC | 0:0 | |
|||
| 24. Ronde | 03.01.2009 | Darlington FC | - | AFC Bournemouth | 2:1 |
Ierland