| 1. Round | 21/08/1965 | Leeds United | - | Sunderland AFC | 1:0 | ||||
| 7. Round | 11/09/1965 | Sunderland AFC | - | Blackburn Rovers | 1:0 | ||||
| 8. Round | 15/09/1965 | Sunderland AFC | - | Aston Villa | 2:0 |  |
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| 9. Round | 18/09/1965 | Blackpool FC | - | Sunderland AFC | 1:2 | |
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| 10. Round | 25/09/1965 | Sunderland AFC | - | Fulham FC | 2:2 | |
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| 11. Round | 06/10/1965 | Tottenham Hotspur | - | Sunderland AFC | 3:0 | ||||
| 12. Round | 09/10/1965 | West Bromwich Albion | - | Sunderland AFC | 4:1 | ||||
| 20. Round | 04/12/1965 | Everton FC | - | Sunderland AFC | 2:0 | ||||
| 28. Round | 29/01/1966 | Sunderland AFC | - | Leeds United | 2:0 | ||||
| 29. Round | 05/02/1966 | Sheffield United | - | Sunderland AFC | 2:2 | ||||
| 30. Round | 12/02/1966 | Liverpool FC | - | Sunderland AFC | 4:0 | ||||
| 31. Round | 19/02/1966 | Sunderland AFC | - | Leicester City | 0:3 | ||||
| 18. Round | 22/02/1966 | Chelsea FC | - | Sunderland AFC | 3:2 | |
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| 32. Round | 26/02/1966 | Blackburn Rovers | - | Sunderland AFC | 2:0 | ||||
| 24. Round | 05/03/1966 | Newcastle United | - | Sunderland AFC | 2:0 |
Scotland