| 3. Runde | 11.12.1999 | Charlton Athletic | - | Swindon Town | 2:1 |  |
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| 4. Runde | 08.01.2000 | Charlton Athletic | - | Queens Park Rangers | 1:0 | ||||
| Achtelfinale | 29.01.2000 | Coventry City | - | Charlton Athletic | 2:3 | ||||
| Viertelfinale | 19.02.2000 | Bolton Wanderers | - | Charlton Athletic | 1:0 |
Irland