| 18. Round | 22/11/1958 | Chelsea FC | - | Arsenal FC | 0:3 |  |
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| 19. Round | 29/11/1958 | Arsenal FC | - | Blackpool FC | 1:4 | ||||
| 20. Round | 06/12/1958 | Portsmouth FC | - | Arsenal FC | 0:1 | ||||
| 22. Round | 20/12/1958 | Arsenal FC | - | Preston North End | 1:2 | ||||
| 28. Round | 07/02/1959 | Manchester City | - | Arsenal FC | 0:0 | ||||
| 30. Round | 21/02/1959 | West Bromwich Albion | - | Arsenal FC | 1:1 | ||||
| 29. Round | 24/02/1959 | Arsenal FC | - | Leeds United | 1:0 | ||||
| 31. Round | 28/02/1959 | Arsenal FC | - | Manchester United | 3:2 | |
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| 32. Round | 07/03/1959 | Wolverhampton Wanderers | - | Arsenal FC | 6:1 | ||||
| 33. Round | 14/03/1959 | Arsenal FC | - | Blackburn Rovers | 1:1 | ||||
| 34. Round | 21/03/1959 | Newcastle United | - | Arsenal FC | 1:0 | ||||
| 38. Round | 04/04/1959 | Nottingham Forest | - | Arsenal FC | 1:1 | ||||
| 39. Round | 11/04/1959 | Arsenal FC | - | Chelsea FC | 1:1 | ||||
| 35. Round | 14/04/1959 | Birmingham City | - | Arsenal FC | 4:1 | ||||
| 40. Round | 18/04/1959 | Blackpool FC | - | Arsenal FC | 1:2 | ||||
| 37. Round | 04/05/1959 | Arsenal FC | - | Birmingham City | 2:1 |
England