| 1. Round | 07/08/1998 | Sunderland AFC | - | Queens Park Rangers | 1:0 |  |
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| 2. Round | 14/08/1998 | Swindon Town | - | Sunderland AFC | 1:1 | ||||
| 8. Round | 11/09/1998 | Wolverhampton Wanderers | - | Sunderland AFC | 1:1 | ||||
| 15. Round | 20/10/1998 | Huddersfield Town | - | Sunderland AFC | 1:1 | ||||
| 17. Round | 31/10/1998 | Bolton Wanderers | - | Sunderland AFC | 0:3 | ||||
| 6. Round | 02/11/1998 | Crewe Alexandra | - | Sunderland AFC | 1:4 | ||||
| 18. Round | 06/11/1998 | Sunderland AFC | - | Grimsby Town | 3:1 | ||||
| 19. Round | 13/11/1998 | Port Vale FC | - | Sunderland AFC | 0:2 | ||||
| 20. Round | 20/11/1998 | Sunderland AFC | - | Barnsley FC | 2:3 |  |
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| 21. Round | 27/11/1998 | Sheffield United | - | Sunderland AFC | 0:4 | ||||
| 22. Round | 04/12/1998 | Sunderland AFC | - | Stockport County | 1:0 | ||||
| 23. Round | 11/12/1998 | Sunderland AFC | - | Port Vale FC | 2:0 | ||||
| 13. Round | 14/12/1998 | Sunderland AFC | - | Crystal Palace | 2:0 | |
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| 24. Round | 18/12/1998 | Birmingham City | - | Sunderland AFC | 0:0 | ||||
| 25. Round | 25/12/1998 | Tranmere Rovers | - | Sunderland AFC | 1:0 | ||||
| 26. Round | 27/12/1998 | Sunderland AFC | - | Crewe Alexandra | 2:0 |
England