| 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 |
| 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 |
| John Thomas Jackson | |
| Born: | 21.12.1876 |
| Place of birth: |
Padiham, 
England |
| Nationality: |
England
|