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