| 1. Round | 23/08/1999 | Barnsley FC | - | Lincoln City | 2:2 | ||||
| 2. Round | 13/09/1999 | Barnsley FC | - | Stockport County | 1:1 |  |
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| 2. Round | 20/09/1999 | Stockport County | - | Barnsley FC | 3:3 aet |  |
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| 3. Round | 11/10/1999 | Bradford City | - | Barnsley FC | 2:3 | |
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| Round of 16 | 29/11/1999 | Tranmere Rovers | - | Barnsley FC | 4:0 |
Germany