| Wednesday 27th August 2008 | |||
| Second Round | |||
| 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 |
| Tuesday 23rd September 2008 | |||
| Third Round | |||
| Arsenal | v | Sheffield United | |
| Aston Villa | v | Queens Park Rangers | |
| Blackburn Rovers | v | Everton | |
| Burnley | v | Fulham | |
| Ipswich Town | v | Wigan Athletic | |
| Leeds United | v | Hartlepool United | |
| Liverpool | v | Crewe Alexandra | |
| Manchester United | v | Middlesbrough | |
| Newcastle United | v | Tottenham Hotspur | |
| Portsmouth | v | Chelsea | |
| Rotherham United | v | Southampton | |
| Stoke City | v | Reading | |
| Sunderland | v | Northampton Town | |
| Swansea City | v | Cardiff City | |
| Watford | v | West Ham United | |