| 3. Round | 01/01/1999 | Swindon Town | - | Barnsley FC | 0:0 | ||||
| 3. Round | 18/01/1999 | Barnsley FC | - | Swindon Town | 3:1 | ||||
| 4. Round | 22/01/1999 | Barnsley FC | - | AFC Bournemouth | 3:1 |  |
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| Round of 16 | 12/02/1999 | Barnsley FC | - | Bristol Rovers | 4:1 | |
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| Quarter-finals | 15/03/1999 | Barnsley FC | - | Tottenham Hotspur | 0:1 |  |
England