| 23. Round | 03/02/1900 | Glossop North End | - | Stoke City | 1:2 | ||||
| 19. Round | 24/02/1900 | Sunderland AFC | - | Glossop North End | 0:0 | ||||
| 9. Round | 27/02/1900 | Glossop North End | - | Blackburn Rovers | 4:2 | ||||
| 26. Round | 03/03/1900 | Blackburn Rovers | - | Glossop North End | 2:2 | ||||
| 15. Round | 14/03/1900 | Newcastle United | - | Glossop North End | 1:0 | ||||
| 28. Round | 17/03/1900 | Glossop North End | - | Bury FC | 0:0 | ||||
| 29. Round | 24/03/1900 | Notts County | - | Glossop North End | 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 | ||||
| 32. Round | 14/04/1900 | Glossop North End | - | Newcastle United | 0:0 | ||||
| 25. Round | 16/04/1900 | Everton FC | - | Glossop North End | 4:1 | ||||
| 24. Round | 24/04/1900 | Glossop North End | - | West Bromwich Albion | 1:1 | ||||
| 34. Round | 28/04/1900 | Glossop North End | - | Liverpool FC | 1:2 |
England