| 1. Round | 01/09/1900 | Preston North End | - | Everton FC | 1:2 | ||||
| 25. Round | 03/09/1900 | Aston Villa | - | Preston North End | 4:0 | ||||
| 2. Round | 08/09/1900 | Sunderland AFC | - | Preston North End | 3:1 | ||||
| 3. Round | 15/09/1900 | Preston North End | - | Derby County | 3:2 |  |
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| 4. Round | 22/09/1900 | Bolton Wanderers | - | Preston North End | 1:1 | ||||
| 5. Round | 29/09/1900 | Preston North End | - | Notts County | 0:1 | ||||
| 31. Round | 04/10/1900 | Nottingham Forest | - | Preston North End | 4:1 | ||||
| 6. Round | 06/10/1900 | The Wednesday FC | - | Preston North End | 0:1 |
England