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| 23/01/1999 | Aston Villa | - | Fulham FC | 0:2 (0:2) | ||
| Barnsley FC | - | AFC Bournemouth | 3:1 (1:0) | |||
| Blackburn Rovers | - | Sunderland AFC | 1:0 (0:0) | |||
| Bristol Rovers | - | Leyton Orient | 3:0 (0:0) | |||
| Everton FC | - | Ipswich Town | 1:0 (1:0) | |||
| Leicester City | - | Coventry City | 0:3 (0:1) | |||
| Newcastle United | - | Bradford City | 3:0 (1:0) | |||
| Portsmouth FC | - | Leeds United | 1:5 (1:2) | |||
| Sheffield Wednesday | - | Stockport County | 2:0 (1:0) | |||
| Swansea City | - | Derby County | 0:1 (0:0) | |||
| Wimbledon FC | - | Tottenham Hotspur | 1:1 (0:0) | |||
| Wrexham AFC | - | Huddersfield Town | 1:1 (1:1) | |||
| 24/01/1999 | Manchester United | - | Liverpool FC | 2:1 (0:1) | ||
| Wolverhampton Wanderers | - | Arsenal FC | 1:2 (1:1) | |||
| 25/01/1999 | Oxford United | - | Chelsea FC | 1:1 (0:0) | ||
| 27/01/1999 | Sheffield United | - | Cardiff City | 4:1 (1:1) | ||
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 02/02/1999 | Tottenham Hotspur | - | Wimbledon FC | 3:0 (1:0) | ||
| 03/02/1999 | Chelsea FC | - | Oxford United | 4:2 (2:1) | ||
| Huddersfield Town | - | Wrexham AFC | 2:1 (2:1) | |||
