| 2. Round | 26/09/1990 | Walsall FC | - | Chelsea FC | 0:5 |  |
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| 2. Round | 10/10/1990 | Chelsea FC | - | Walsall FC | 4:1 | |
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| 3. Round | 06/11/1990 | Portsmouth FC | - | Chelsea FC | 2:3 | ||||
| Round of 16 | 28/11/1990 | Oxford United | - | Chelsea FC | 1:2 | ||||
| Quarter-finals | 16/01/1991 | Chelsea FC | - | Tottenham Hotspur | 0:0 | ||||
| Quarter-finals | 23/01/1991 | Tottenham Hotspur | - | Chelsea FC | 0:3 | |
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| Semi-finals | 24/02/1991 | Chelsea FC | - | Sheffield Wednesday | 0:2 | ||||
| Semi-finals | 27/02/1991 | Sheffield Wednesday | - | Chelsea FC | 3:1 |
England