1. Round | 09/08/2008 | Scunthorpe United | - | Leeds United | 1:2 | ||||
2. Round | 16/08/2008 | Walsall FC | - | Scunthorpe United | 2:1 | ||||
3. Round | 23/08/2008 | Scunthorpe United | - | Peterborough United | 1:0 | ||||
6. Round | 13/09/2008 | Scunthorpe United | - | Carlisle United | 2:1 | ||||
7. Round | 20/09/2008 | Hereford United | - | Scunthorpe United | 1:2 | ||||
8. Round | 27/09/2008 | Scunthorpe United | - | Yeovil Town | 2:0 | ||||
9. Round | 04/10/2008 | Leyton Orient | - | Scunthorpe United | 2:2 | ||||
10. Round | 11/10/2008 | Scunthorpe United | - | Crewe Alexandra | 3:0 | ||||
12. Round | 21/10/2008 | Scunthorpe United | - | Southend United | 1:1 | ||||
13. Round | 25/10/2008 | Scunthorpe United | - | Millwall FC | 3:2 | ||||
14. Round | 28/10/2008 | Oldham Athletic | - | Scunthorpe United | 3:0 | ||||
15. Round | 01/11/2008 | Scunthorpe United | - | Swindon Town | 3:3 | ||||
16. Round | 14/11/2008 | Bristol Rovers | - | Scunthorpe United | 1:2 | ||||
17. Round | 22/11/2008 | Scunthorpe United | - | Leicester City | 1:2 | ||||
18. Round | 25/11/2008 | Tranmere Rovers | - | Scunthorpe United | 2:0 | ||||
20. Round | 13/12/2008 | Scunthorpe United | - | Northampton Town | 4:4 |