| 1. Runde | 10.08.1999 | Darlington FC | - | Bolton Wanderers | 1:1 |  |
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| 1. Runde | 24.08.1999 | Bolton Wanderers | - | Darlington FC | 5:3 |  |
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| 2. Runde | 14.09.1999 | Gillingham FC | - | Bolton Wanderers | 1:4 | ||||
| 2. Runde | 21.09.1999 | Bolton Wanderers | - | Gillingham FC | 2:0 | ||||
| 3. Runde | 13.10.1999 | Derby County | - | Bolton Wanderers | 1:2 | ||||
| Achtelfinale | 30.11.1999 | Bolton Wanderers | - | Sheffield Wednesday | 1:0 | |
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| Viertelfinale | 14.12.1999 | Bolton Wanderers | - | Wimbledon FC | 2:1 | ||||
| Halbfinale | 12.01.2000 | Bolton Wanderers | - | Tranmere Rovers | 0:1 | ||||
| Halbfinale | 26.01.2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |
Jamaika