| 3. Round | 01/09/1923 | Chelsea FC | - | Blackburn Rovers | 2:0 |  |
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| 4. Round | 03/09/1923 | Tottenham Hotspur | - | Chelsea FC | 0:1 | ||||
| 6. Round | 15/09/1923 | Aston Villa | - | Chelsea FC | 0:0 | ||||
| 7. Round | 22/09/1923 | Chelsea FC | - | Sheffield United | 1:1 | ||||
| 9. Round | 06/10/1923 | Chelsea FC | - | Cardiff City | 1:2 | ||||
| 37. Round | 12/04/1924 | Newcastle United | - | Chelsea FC | 2:1 |
England