| 3. Runde | 02.01.1999 | Rushden & Diamonds FC | - | Leeds United | 0:0 |  |
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| 3. Runde | 13.01.1999 | Leeds United | - | Rushden & Diamonds FC | 3:1 | ||||
| 4. Runde | 23.01.1999 | Portsmouth FC | - | Leeds United | 1:5 | ||||
| Achtelfinale | 13.02.1999 | Leeds United | - | Tottenham Hotspur | 1:1 |  |
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| Achtelfinale | 24.02.1999 | Tottenham Hotspur | - | Leeds United | 2:0 |
England