| 1. Round | 18/08/1989 | Manchester United | - | Arsenal FC | 4:1 | ||||
| 2. Round | 21/08/1989 | Arsenal FC | - | Coventry City | 2:0 |  |
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| 3. Round | 25/08/1989 | Arsenal FC | - | Wimbledon FC | 0:0 | ||||
| 5. Round | 08/09/1989 | Arsenal FC | - | Sheffield Wednesday | 5:0 | |
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| 6. Round | 15/09/1989 | Nottingham Forest | - | Arsenal FC | 1:2 | |
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| 7. Round | 22/09/1989 | Arsenal FC | - | Charlton Athletic | 1:0 | |
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| 9. Round | 14/10/1989 | Arsenal FC | - | Manchester City | 4:0 | ||||
| 13. Round | 10/11/1989 | Millwall FC | - | Arsenal FC | 1:2 | ||||
| 14. Round | 17/11/1989 | Arsenal FC | - | Queens Park Rangers | 3:0 | ||||
| 16. Round | 02/12/1989 | Arsenal FC | - | Manchester United | 1:0 | ||||
| 17. Round | 08/12/1989 | Coventry City | - | Arsenal FC | 0:1 | ||||
| 18. Round | 15/12/1989 | Arsenal FC | - | Luton Town | 3:2 | |
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| 19. Round | 25/12/1989 | Southampton FC | - | Arsenal FC | 1:0 | ||||
| 24. Round | 26/02/1990 | Charlton Athletic | - | Arsenal FC | 0:0 | ||||
| 29. Round | 09/03/1990 | Manchester City | - | Arsenal FC | 1:1 | |
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| 37. Round | 27/04/1990 | Arsenal FC | - | Millwall FC | 2:0 | ||||
| 35. Round | 01/05/1990 | Arsenal FC | - | Southampton FC | 2:1 |
England