| 2. Round | 14/08/1998 | Swindon Town | - | Sunderland AFC | 1:1 | ||||
| 3. Round | 21/08/1998 | Sunderland AFC | - | Tranmere Rovers | 5:0 |  |
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| 5. Round | 24/08/1998 | Sunderland AFC | - | Watford FC | 4:1 | ||||
| 4. Round | 28/08/1998 | Ipswich Town | - | Sunderland AFC | 0:2 | |
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| 7. Round | 07/09/1998 | Sunderland AFC | - | Bristol City | 1:1 | ||||
| 9. Round | 18/09/1998 | Sunderland AFC | - | Oxford United | 7:0 | ||||
| 10. Round | 25/09/1998 | Portsmouth FC | - | Sunderland AFC | 1:1 | ||||
| 14. Round | 17/10/1998 | West Bromwich Albion | - | Sunderland AFC | 2:3 | ||||
| 17. Round | 31/10/1998 | Bolton Wanderers | - | Sunderland AFC | 0:3 | |
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| 6. Round | 02/11/1998 | Crewe Alexandra | - | Sunderland AFC | 1:4 |
England