| 25. Round | 08/02/1939 | Brentford FC | - | Aston Villa | 2:4 | ||||
| 28. Round | 11/02/1939 | Derby County | - | Brentford FC | 1:2 |  |
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| 29. Round | 18/02/1939 | Brentford FC | - | Stoke City | 1:0 | |
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| 21. Round | 22/02/1939 | Brentford FC | - | Portsmouth FC | 2:0 | ||||
| 30. Round | 25/02/1939 | Chelsea FC | - | Brentford FC | 1:3 | |
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| 31. Round | 04/03/1939 | Brentford FC | - | Charlton Athletic | 1:0 | ||||
| 32. Round | 11/03/1939 | Bolton Wanderers | - | Brentford FC | 1:1 | ||||
| 33. Round | 18/03/1939 | Brentford FC | - | Leeds United | 0:1 | ||||
| 34. Round | 25/03/1939 | Liverpool FC | - | Brentford FC | 1:0 | ||||
| 35. Round | 01/04/1939 | Brentford FC | - | Leicester City | 2:0 | ||||
| 36. Round | 07/04/1939 | Brentford FC | - | Preston North End | 3:1 | |
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| 37. Round | 08/04/1939 | Middlesbrough FC | - | Brentford FC | 3:1 | |
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| 38. Round | 10/04/1939 | Preston North End | - | Brentford FC | 2:0 | ||||
| 39. Round | 15/04/1939 | Brentford FC | - | Birmingham FC | 0:1 | ||||
| 40. Round | 22/04/1939 | Manchester United | - | Brentford FC | 3:0 | ||||
| 41. Round | 29/04/1939 | Brentford FC | - | Blackpool FC | 1:1 | |
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| 42. Round | 06/05/1939 | Arsenal FC | - | Brentford FC | 2:0 |
England