| 4. Round | 23/09/1899 | Nottingham Forest | - | Stoke City | 1:0 | ||||
| 8. Round | 21/10/1899 | Nottingham Forest | - | Blackburn Rovers | 3:2 |  |
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| 13. Round | 25/11/1899 | Sheffield United | - | Nottingham Forest | 3:0 | ||||
| 14. Round | 02/12/1899 | Nottingham Forest | - | Newcastle United | 1:0 | ||||
| 21. Round | 13/01/1900 | Nottingham Forest | - | Glossop North End | 5:0 | ||||
| 28. Round | 17/03/1900 | Nottingham Forest | - | Notts County | 0:3 | ||||
| 23. Round | 17/04/1900 | Nottingham Forest | - | Sunderland AFC | 1:3 | |
England