| 3. Round | 16/09/1899 | Sunderland AFC | - | Burnley FC | 2:1 |  |
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| 4. Round | 23/09/1899 | Preston North End | - | Sunderland AFC | 0:1 | ||||
| 5. Round | 30/09/1899 | Sunderland AFC | - | Nottingham Forest | 1:0 | ||||
| 33. Round | 02/10/1899 | Sheffield United | - | Sunderland AFC | 2:2 | |
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| 6. Round | 07/10/1899 | Glossop North End | - | Sunderland AFC | 0:2 | |
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| 7. Round | 14/10/1899 | Sunderland AFC | - | Stoke City | 3:0 | ||||
| 10. Round | 04/11/1899 | Sunderland AFC | - | Everton FC | 1:0 | ||||
| 11. Round | 11/11/1899 | Blackburn Rovers | - | Sunderland AFC | 1:2 | |
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| 13. Round | 25/11/1899 | Bury FC | - | Sunderland AFC | 2:0 | ||||
| 14. Round | 02/12/1899 | Sunderland AFC | - | Notts County | 5:0 | ||||
| 15. Round | 09/12/1899 | Manchester City | - | Sunderland AFC | 2:1 | |
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| 17. Round | 23/12/1899 | Newcastle United | - | Sunderland AFC | 2:4 | ||||
| 8. Round | 26/12/1899 | Wolverhampton Wanderers | - | Sunderland AFC | 1:0 | ||||
| 18. Round | 30/12/1899 | Aston Villa | - | Sunderland AFC | 4:2 | ||||
| 25. Round | 01/01/1900 | Sunderland AFC | - | Wolverhampton Wanderers | 1:2 |
England