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| U | Sunderland AFC | - | Leicester City | 1:2 (0:1) | ||
| R | Leicester City | - | Sunderland AFC | 1:1 (0:1) | ||
| U: 26.01.1999 | R: 17.02.1999 | Winnaars: Leicester City | ||||
| U | Tottenham Hotspur | - | Wimbledon FC | 0:0 (0:0) | ||
| R | Wimbledon FC | - | Tottenham Hotspur | 0:1 (0:1) | ||
| U: 27.01.1999 | R: 16.02.1999 | Winnaars: Tottenham Hotspur | ||||
