| Red | Clubs | VS Club | Date | Sections | |
|---|---|---|---|---|---|
| 1 | Burnley | Chelsea | 12-11-2008 | Fourth Round | Match details |
| 1 | Cardiff City | Swansea City | 23-09-2008 | Third Round | Match details |
| 1 | Middlesbrough | Manchester United | 23-09-2008 | Third Round | Match details |
| 1 | Macclesfield Town | West Ham United | 27-08-2008 | Second Round | Match details |
| 1 | Bolton Wanderers | Northampton Town | 26-08-2008 | Second Round | Match details |
| 1 | Brighton & Hove Albion | Barnet | 12-08-2008 | First Round | Match details |
| 1 | Brentford | Swansea City | 12-08-2008 | First Round | Match details |
| 1 | Stockport County | Leicester City | 12-08-2008 | First Round | Match details |
| 1 | Walsall | Darlington | 12-08-2008 | First Round | Match details |
| 1 | Macclesfield Town | Blackpool | 12-08-2008 | First Round | Match details |
