| 1. Round | 02/09/1899 | Glossop North End | - | Burnley FC | 2:0 | ||||
| 33. Round | 04/09/1899 | Aston Villa | - | Glossop North End | 9:0 | ||||
| 2. Round | 09/09/1899 | Preston North End | - | Glossop North End | 1:0 | ||||
| 3. Round | 16/09/1899 | Glossop North End | - | Nottingham Forest | 3:0 | ||||
| 5. Round | 30/09/1899 | Stoke City | - | Glossop North End | 1:0 | ||||
| 7. Round | 14/10/1899 | West Bromwich Albion | - | Glossop North End | 3:3 |  |
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| 8. Round | 21/10/1899 | Glossop North End | - | Everton FC | 1:1 | |
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| 11. Round | 11/11/1899 | Bury FC | - | Glossop North End | 2:1 | |
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| 12. Round | 18/11/1899 | Glossop North End | - | Notts County | 0:0 | ||||
| 13. Round | 25/11/1899 | Manchester City | - | Glossop North End | 4:1 | ||||
| 19. Round | 24/02/1900 | Sunderland AFC | - | Glossop North End | 0:0 | ||||
| 9. Round | 27/02/1900 | Glossop North End | - | Blackburn Rovers | 4:2 | |
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| 26. Round | 03/03/1900 | Blackburn Rovers | - | Glossop North End | 2:2 | ||||
| 28. Round | 17/03/1900 | Glossop North End | - | Bury FC | 0:0 | ||||
| 30. Round | 31/03/1900 | Glossop North End | - | Manchester City | 0:2 | ||||
| 27. Round | 13/04/1900 | Glossop North End | - | Derby County | 1:3 | ||||
| 34. Round | 28/04/1900 | Glossop North End | - | Liverpool FC | 1:2 |
Scotland