| 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 |  |
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| 4. Round | 23/09/1899 | Wolverhampton Wanderers | - | Glossop North End | 4:0 | ||||
| 5. Round | 30/09/1899 | Stoke City | - | Glossop North End | 1:0 | ||||
| 6. Round | 07/10/1899 | Glossop North End | - | Sunderland AFC | 0:2 | ||||
| 7. Round | 14/10/1899 | West Bromwich Albion | - | Glossop North End | 3:3 | ||||
| 13. Round | 25/11/1899 | Manchester City | - | Glossop North End | 4:1 | ||||
| 18. Round | 30/12/1899 | Burnley FC | - | Glossop North End | 3:1 | ||||
| 20. Round | 06/01/1900 | Glossop North End | - | Preston North End | 0:2 | ||||
| 21. Round | 13/01/1900 | Nottingham Forest | - | Glossop North End | 5:0 | ||||
| 22. Round | 20/01/1900 | Glossop North End | - | Wolverhampton Wanderers | 2:3 |
England