| 1. Ronde | 19.08.1989 | Wimbledon FC | - | Chelsea FC | 0:1 |  |
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| 2. Ronde | 22.08.1989 | Chelsea FC | - | Queens Park Rangers | 1:1 | ||||
| 4. Ronde | 29.08.1989 | Charlton Athletic | - | Chelsea FC | 3:0 | ||||
| 5. Ronde | 09.09.1989 | Chelsea FC | - | Nottingham Forest | 2:2 |  |
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| 18. Ronde | 16.12.1989 | Chelsea FC | - | Liverpool FC | 2:5 | |
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| 28. Ronde | 03.03.1990 | Southampton FC | - | Chelsea FC | 2:3 | |
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| 29. Ronde | 10.03.1990 | Chelsea FC | - | Norwich City | 0:0 | ||||
| 30. Ronde | 17.03.1990 | Arsenal FC | - | Chelsea FC | 0:1 | ||||
| 31. Ronde | 21.03.1990 | Manchester City | - | Chelsea FC | 1:1 | |
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| 32. Ronde | 31.03.1990 | Chelsea FC | - | Derby County | 1:1 | ||||
| 33. Ronde | 07.04.1990 | Chelsea FC | - | Luton Town | 1:0 | |
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| 34. Ronde | 14.04.1990 | Aston Villa | - | Chelsea FC | 1:0 | ||||
| 35. Ronde | 16.04.1990 | Chelsea FC | - | Crystal Palace | 3:0 | ||||
| 36. Ronde | 21.04.1990 | Liverpool FC | - | Chelsea FC | 4:1 | ||||
| 37. Ronde | 28.04.1990 | Chelsea FC | - | Everton FC | 2:1 |
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