| 3. Ronde | 16.09.1899 | Sunderland AFC | - | Burnley FC | 2:1 |  |
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| 4. Ronde | 23.09.1899 | Preston North End | - | Sunderland AFC | 0:1 | ||||
| 5. Ronde | 30.09.1899 | Sunderland AFC | - | Nottingham Forest | 1:0 | ||||
| 33. Ronde | 02.10.1899 | Sheffield United | - | Sunderland AFC | 2:2 | |
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| 6. Ronde | 07.10.1899 | Glossop North End | - | Sunderland AFC | 0:2 | |
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| 7. Ronde | 14.10.1899 | Sunderland AFC | - | Stoke City | 3:0 | ||||
| 10. Ronde | 04.11.1899 | Sunderland AFC | - | Everton FC | 1:0 | ||||
| 11. Ronde | 11.11.1899 | Blackburn Rovers | - | Sunderland AFC | 1:2 | |
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| 13. Ronde | 25.11.1899 | Bury FC | - | Sunderland AFC | 2:0 | ||||
| 14. Ronde | 02.12.1899 | Sunderland AFC | - | Notts County | 5:0 | ||||
| 15. Ronde | 09.12.1899 | Manchester City | - | Sunderland AFC | 2:1 | |
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| 17. Ronde | 23.12.1899 | Newcastle United | - | Sunderland AFC | 2:4 | ||||
| 8. Ronde | 26.12.1899 | Wolverhampton Wanderers | - | Sunderland AFC | 1:0 | ||||
| 18. Ronde | 30.12.1899 | Aston Villa | - | Sunderland AFC | 4:2 | ||||
| 25. Ronde | 01.01.1900 | Sunderland AFC | - | Wolverhampton Wanderers | 1:2 |
Engeland