| 24. Round | 31/12/1987 | Luton Town | - | Chelsea FC | 3:0 | ||||
| 25. Round | 01/01/1988 | Chelsea FC | - | Tottenham Hotspur | 0:0 | ||||
| 26. Round | 15/01/1988 | Sheffield Wednesday | - | Chelsea FC | 3:0 | ||||
| 27. Round | 22/01/1988 | Chelsea FC | - | Portsmouth FC | 0:0 | ||||
| 28. Round | 05/02/1988 | Nottingham Forest | - | Chelsea FC | 3:2 | ||||
| 29. Round | 12/02/1988 | Chelsea FC | - | Manchester United | 1:2 | ||||
| 32. Round | 04/03/1988 | Coventry City | - | Chelsea FC | 3:3 | ||||
| 33. Round | 11/03/1988 | Chelsea FC | - | Everton FC | 0:0 | ||||
| 34. Round | 18/03/1988 | Oxford United | - | Chelsea FC | 4:4 |  |
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| 35. Round | 25/03/1988 | Chelsea FC | - | Southampton FC | 0:1 | ||||
| 30. Round | 28/03/1988 | Chelsea FC | - | Watford FC | 1:1 | ||||
| 36. Round | 01/04/1988 | Chelsea FC | - | Arsenal FC | 1:1 | ||||
| 38. Round | 08/04/1988 | Chelsea FC | - | Derby County | 1:0 | ||||
| 39. Round | 22/04/1988 | Wimbledon FC | - | Chelsea FC | 2:2 | ||||
| 40. Round | 29/04/1988 | Chelsea FC | - | Liverpool FC | 1:1 | ||||
| 41. Round | 01/05/1988 | West Ham United | - | Chelsea FC | 4:1 | ||||
| 42. Round | 06/05/1988 | Chelsea FC | - | Charlton Athletic | 1:1 |
England