| 21. Round | 27/11/1998 | Sheffield United | - | Sunderland AFC | 0:4 | ||||
| 23. Round | 11/12/1998 | Sunderland AFC | - | Port Vale FC | 2:0 | ||||
| 13. Round | 14/12/1998 | Sunderland AFC | - | Crystal Palace | 2:0 | ||||
| 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 |  |
|||
| 27. Round | 08/01/1999 | Queens Park Rangers | - | Sunderland AFC | 2:2 | ||||
| 29. Round | 29/01/1999 | Watford FC | - | Sunderland AFC | 2:1 | ||||
| 33. Round | 26/02/1999 | Oxford United | - | Sunderland AFC | 0:0 | ||||
| 35. Round | 05/03/1999 | Sunderland AFC | - | Norwich City | 1:0 | ||||
| 45. Round | 30/04/1999 | Stockport County | - | Sunderland AFC | 0:1 |
England