| 12. Round | 05/10/1968 | Chelsea FC | - | Ipswich Town | 3:1 | ||||
| 13. Round | 09/10/1968 | Sheffield Wednesday | - | Chelsea FC | 1:1 | ||||
| 29. Round | 01/02/1969 | Southampton FC | - | Chelsea FC | 5:0 | ||||
| 26. Round | 05/03/1969 | Chelsea FC | - | Stoke City | 1:0 | ||||
| 33. Round | 08/03/1969 | West Bromwich Albion | - | Chelsea FC | 0:3 |  |
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| 32. Round | 10/03/1969 | Chelsea FC | - | Coventry City | 2:1 | |
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| 34. Round | 15/03/1969 | Chelsea FC | - | Manchester United | 3:2 | |
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| 35. Round | 22/03/1969 | Tottenham Hotspur | - | Chelsea FC | 1:0 | ||||
| 36. Round | 29/03/1969 | Everton FC | - | Chelsea FC | 1:2 | |
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| 38. Round | 04/04/1969 | Chelsea FC | - | Newcastle United | 1:1 | |
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| 37. Round | 05/04/1969 | Chelsea FC | - | Burnley FC | 2:3 | ||||
| 39. Round | 08/04/1969 | Nottingham Forest | - | Chelsea FC | 1:2 | |
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| 40. Round | 12/04/1969 | West Ham United | - | Chelsea FC | 0:0 | ||||
| 41. Round | 14/04/1969 | Chelsea FC | - | Arsenal FC | 2:1 | ||||
| 42. Round | 19/04/1969 | Chelsea FC | - | Queens Park Rangers | 2:1 |
England