| 1. Journée | 02.09.1899 | Glossop North End | - | Burnley FC | 2:0 | ||||
| 33. Journée | 04.09.1899 | Aston Villa | - | Glossop North End | 9:0 | ||||
| 2. Journée | 09.09.1899 | Preston North End | - | Glossop North End | 1:0 | ||||
| 3. Journée | 16.09.1899 | Glossop North End | - | Nottingham Forest | 3:0 |  |
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| 4. Journée | 23.09.1899 | Wolverhampton Wanderers | - | Glossop North End | 4:0 | ||||
| 5. Journée | 30.09.1899 | Stoke City | - | Glossop North End | 1:0 | ||||
| 6. Journée | 07.10.1899 | Glossop North End | - | Sunderland AFC | 0:2 | ||||
| 7. Journée | 14.10.1899 | West Bromwich Albion | - | Glossop North End | 3:3 | ||||
| 13. Journée | 25.11.1899 | Manchester City | - | Glossop North End | 4:1 | ||||
| 18. Journée | 30.12.1899 | Burnley FC | - | Glossop North End | 3:1 | ||||
| 20. Journée | 06.01.1900 | Glossop North End | - | Preston North End | 0:2 | ||||
| 21. Journée | 13.01.1900 | Nottingham Forest | - | Glossop North End | 5:0 | ||||
| 22. Journée | 20.01.1900 | Glossop North End | - | Wolverhampton Wanderers | 2:3 |
Angleterre