| 3. Round | 03/09/1938 | Sunderland AFC | - | Grimsby Town | 1:1 | ||||
| 22. Round | 27/12/1938 | Wolverhampton Wanderers | - | Grimsby Town | 5:0 | ||||
| 29. Round | 18/02/1939 | Grimsby Town | - | Middlesbrough FC | 0:2 | ||||
| 28. Round | 21/02/1939 | Grimsby Town | - | Arsenal FC | 2:1 | ||||
| 30. Round | 25/02/1939 | Birmingham FC | - | Grimsby Town | 1:1 | ||||
| 31. Round | 07/03/1939 | Grimsby Town | - | Stoke City | 3:1 | ||||
| 32. Round | 11/03/1939 | Chelsea FC | - | Grimsby Town | 5:1 | ||||
| 33. Round | 18/03/1939 | Grimsby Town | - | Preston North End | 1:1 | ||||
| 34. Round | 29/03/1939 | Charlton Athletic | - | Grimsby Town | 3:1 | ||||
| 35. Round | 01/04/1939 | Grimsby Town | - | Bolton Wanderers | 1:1 | ||||
| 39. Round | 15/04/1939 | Grimsby Town | - | Liverpool FC | 2:1 | ||||
| 41. Round | 19/04/1939 | Portsmouth FC | - | Grimsby Town | 2:1 | ||||
| 40. Round | 22/04/1939 | Leicester City | - | Grimsby Town | 0:2 |  |
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| 42. Round | 06/05/1939 | Grimsby Town | - | Everton FC | 3:0 |
England