| 1. Round | 11/08/1998 | Scarborough FC | - | Barnsley FC | 0:1 | ||||
| 1. Round | 17/08/1998 | Barnsley FC | - | Scarborough FC | 3:0 | ||||
| 2. Round | 14/09/1998 | Barnsley FC | - | Reading FC | 3:0 | ||||
| 2. Round | 22/09/1998 | Reading FC | - | Barnsley FC | 1:1 | ||||
| 3. Round | 26/10/1998 | Barnsley FC | - | AFC Bournemouth | 2:1 | ||||
| Round of 16 | 09/11/1998 | Luton Town | - | Barnsley FC | 1:0 |
Netherlands