| Tuesday 24th September 2002 | |||
| Ipswich Town | 3-1 | Brighton and Hove A | |
| Tuesday 1st October 2002 | |||
| Brentford | 1-4 | Middlesbrough | |
| Cambridge United | 0-7 | Sunderland | |
| Charlton Athletic | 0-0 | Oxford United | aet |
| (Oxford United won on penalties) | |||
| Chesterfield | 1-1 | West Ham United | aet |
| (West Ham United won on penalties) | |||
| Huddersfield Town | 0-1 | Burnley | aet |
| Macclesfield Town | 1-2 | Preston North End | |
| Manchester City | 3-2 | Crewe Alexandra | |
| Portsmouth | 1-3 | Wimbledon | |
| Rotherham United | 4-4 | Wolverhampton Wndrs | aet |
| (Rotherham United won on penalties) | |||
| Sheffield United | 4-1 | Wycombe Wanderers | |
| Stockport County | 1-2 | Gillingham | aet |
| Tottenham Hotspur | 1-0 | Cardiff City | |
| Wrexham | 0-3 | Everton | |
| Wednesday 2nd October 2002 | |||
| Aston Villa | 3-0 | Luton Town | |
| Bolton Wanderers | 0-1 | Bury | |
| Coventry City | 8-0 | Rushden and Diamonds | |
| Crystal Palace | 7-0 | Cheltenham Town | |
| Derby County | 1-2 | Oldham Athletic | aet |
| Leyton Orient | 2-3 | Birmingham City | |
| Nottingham Forest | 1-2 | Walsall | |
| Sheffield Wednesday | 1-2 | Leicester City | aet |
| Southampton | 6-1 | Tranmere Rovers | |
| Wigan Athletic | 3-1 | West Bromwich Albion | |
