| Tuesday 26th August 2008 | |||
| Bolton Wanderers | 1-2 | Northampton Town | |
| Burnley | 3-0 | Oldham Athletic | |
| Cardiff City | 2-1 | Milton Keynes Dons | |
| Cheltenham Town | 2-3 | Stoke City | |
| Coventry City | 2-3 | Newcastle United | aet |
| Crewe Alexandra | 2-1 | Bristol City | |
| Hartlepool United | 3-1 | West Bromwich Albion | aet |
| Ipswich Town | 2-1 | Colchester United | |
| Leeds United | 4-0 | Crystal Palace | |
| Middlesbrough | 5-1 | Yeovil Town | |
| Preston North End | 0-1 | Derby County | |
| Queens Park Rangers | 4-0 | Carlisle United | |
| Reading | 5-1 | Luton Town | |
| Rotherham United | 0-0 | Wolverhampton Wndrs | aet |
| (Rotherham United won on penalties) | |||
| Southampton | 2-0 | Birmingham City | |
| Swansea City | 2-1 | Hull City | aet |
| Watford | 2-1 | Darlington | aet |
| Wigan Athletic | 4-0 | Notts County | |
| Wednesday 27th August 2008 | |||
| Blackburn Rovers | 4-1 | Grimsby Town | |
| Fulham | 3-2 | Leicester City | |
| Huddersfield Town | 1-2 | Sheffield United | |
| Nottingham Forest | 1-2 | Sunderland | aet |
| West Ham United | 4-1 | Macclesfield Town | aet |
| Wednesday 24th September 2008 | |||
| Brighton and Hove A | 2-2 | Manchester City | aet |
| (Brighton and Hove A won on penalties) | |||
