| 1. Jornada | 02.09.1899 | Glossop North End | - | Burnley FC | 2:0 | ||||
| 33. Jornada | 04.09.1899 | Aston Villa | - | Glossop North End | 9:0 | ||||
| 2. Jornada | 09.09.1899 | Preston North End | - | Glossop North End | 1:0 | ||||
| 3. Jornada | 16.09.1899 | Glossop North End | - | Nottingham Forest | 3:0 | ||||
| 5. Jornada | 30.09.1899 | Stoke City | - | Glossop North End | 1:0 | ||||
| 6. Jornada | 07.10.1899 | Glossop North End | - | Sunderland | 0:2 | ||||
| 7. Jornada | 14.10.1899 | West Bromwich Albion | - | Glossop North End | 3:3 | ||||
| 8. Jornada | 21.10.1899 | Glossop North End | - | Everton | 1:1 | ||||
| 11. Jornada | 11.11.1899 | Bury FC | - | Glossop North End | 2:1 | ||||
| 12. Jornada | 18.11.1899 | Glossop North End | - | Notts County | 0:0 | ||||
| 13. Jornada | 25.11.1899 | Manchester City | - | Glossop North End | 4:1 | ||||
| 14. Jornada | 02.12.1899 | Glossop North End | - | Sheffield United | 2:2 | ||||
| 10. Jornada | 26.12.1899 | Derby County | - | Glossop North End | 4:1 | ||||
| 18. Jornada | 30.12.1899 | Burnley FC | - | Glossop North End | 3:1 | ||||
| 20. Jornada | 06.01.1900 | Glossop North End | - | Preston North End | 0:2 |
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