| 1. Round | 19/08/1995 | Chelsea FC | - | Everton FC | 0:0 |  |
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| 2. Round | 23/08/1995 | Nottingham Forest | - | Chelsea FC | 0:0 | ||||
| 3. Round | 26/08/1995 | Middlesbrough FC | - | Chelsea FC | 2:0 | |
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| 4. Round | 30/08/1995 | Chelsea FC | - | Coventry City | 2:2 | |
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| 5. Round | 11/09/1995 | West Ham United | - | Chelsea FC | 1:3 | |
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| 6. Round | 16/09/1995 | Chelsea FC | - | Southampton FC | 3:0 |  |
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| 7. Round | 23/09/1995 | Newcastle United | - | Chelsea FC | 2:0 | |
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| 8. Round | 30/09/1995 | Chelsea FC | - | Arsenal FC | 1:0 | ||||
| 10. Round | 21/10/1995 | Chelsea FC | - | Manchester United | 1:4 |  |
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| 11. Round | 28/10/1995 | Blackburn Rovers | - | Chelsea FC | 3:0 | ||||
| 25. Round | 04/02/1996 | Chelsea FC | - | Middlesbrough FC | 5:0 | |
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| 26. Round | 10/02/1996 | Coventry City | - | Chelsea FC | 1:0 | ||||
| 27. Round | 17/02/1996 | Chelsea FC | - | West Ham United | 1:2 |
England