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| 08.01.2000 | Aston Villa | - | Southampton FC | 1:0 (1:0) | ||
| Charlton Athletic | - | Queens Park Rangers | 1:0 (0:0) | |||
| Coventry City | - | Burnley FC | 3:0 (1:0) | |||
| Everton FC | - | Birmingham City | 2:0 (0:0) | |||
| Fulham FC | - | Wimbledon FC | 3:0 (2:0) | |||
| Grimsby Town | - | Bolton Wanderers | 0:2 (0:1) | |||
| Newcastle United | - | Sheffield United | 4:1 (1:1) | |||
| Plymouth Argyle | - | Preston North End | 0:3 (0:1) | |||
| Sheffield Wednesday | - | Wolverhampton Wanderers | 1:1 (1:0) | |||
| Tranmere Rovers | - | Sunderland AFC | 1:0 (1:0) | |||
| Wrexham AFC | - | Cambridge United | 1:2 (1:1) | |||
| 09.01.2000 | Arsenal FC | - | Leicester City | 0:0 (0:0) | ||
| Manchester City | - | Leeds United | 2:5 (2:3) | |||
| 10.01.2000 | Liverpool FC | - | Blackburn Rovers | 0:1 (0:0) | ||
| 11.01.2000 | Gillingham FC | - | Bradford City | 3:1 (1:0) | ||
| 19.01.2000 | Chelsea FC | - | Nottingham Forest | 2:0 (0:0) | ||
| Entscheidungsspiele | ||||||
|---|---|---|---|---|---|---|
| 18.01.2000 | Wolverhampton Wanderers | - | Sheffield Wednesday | 3:4 (0:0, 0:0, 0:0) i.E. | ||
| 19.01.2000 | Leicester City | - | Arsenal FC | 6:5 (0:0, 0:0, 0:0) i.E. | ||
