| Tuesday 27th October 1998 | |||
| Barnsley | 2-1 | Bournemouth | |
| Charlton Athletic | 1-2 | Leicester City | |
| Liverpool | 3-1 | Fulham | |
| Luton Town | 2-0 | Coventry City | |
| Northampton Town | 1-3 | Tottenham Hotspur | |
| Norwich City | 1-1 | Bolton Wanderers | aet |
| (Bolton Wanderers won on penalties) | |||
| Nottingham Forest | 3-3 | Cambridge United | aet |
| (Nottingham Forest won on penalties) | |||
| Sunderland | 2-1 | Grimsby Town | aet |
| Tranmere Rovers | 0-1 | Newcastle United | |
| Wednesday 28th October 1998 | |||
| Birmingham City | 1-2 | Wimbledon | |
| Chelsea | 4-1 | Aston Villa | |
| Crewe Alexandra | 0-1 | Blackburn Rovers | |
| Derby County | 1-2 | Arsenal | |
| Leeds United | 1-0 | Bradford City | |
| Manchester United | 2-0 | Bury | aet |
| Middlesbrough | 2-3 | Everton | aet |
