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| H | Tottenham Hotspur | - | Burnley FC | 4:1 (0:1) | ||
| R | Burnley FC | - | Tottenham Hotspur | 3:2 (1:0, 3:0) n.V. | ||
| H: 06.01.2009 20:45 | R: 21.01.2009 20:45 | Sieger: Tottenham Hotspur | ||||
| H | Derby County | - | Manchester United | 1:0 (1:0) | ||
| R | Manchester United | - | Derby County | 4:2 (3:0) | ||
| H: 07.01.2009 20:45 | R: 20.01.2009 21:00 | Sieger: Manchester United | ||||
