| 1. Runde | 24.08.1999 | Barnsley FC | - | Lincoln City | 2:2 | ||||
| 2. Runde | 14.09.1999 | Barnsley FC | - | Stockport County | 1:1 |  |
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| 2. Runde | 21.09.1999 | Stockport County | - | Barnsley FC | 3:3 n.V. |  |
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| 3. Runde | 12.10.1999 | Bradford City | - | Barnsley FC | 2:3 | |
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| Achtelfinale | 30.11.1999 | Tranmere Rovers | - | Barnsley FC | 4:0 |
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