| 1er tour | 10.08.1999 | Lincoln City | - | Barnsley FC | 2:4 | ||||
| 1er tour | 24.08.1999 | Barnsley FC | - | Lincoln City | 2:2 | ||||
| 2e tour | 14.09.1999 | Barnsley FC | - | Stockport County | 1:1 | ||||
| 2e tour | 21.09.1999 | Stockport County | - | Barnsley FC | 3:3 ap |  |
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| tour des 16 | 30.11.1999 | Tranmere Rovers | - | Barnsley FC | 4:0 |
Macédoine du Nord