| 2. Round | 17/11/1965 | Wiener Sport-Club | - | Chelsea FC | 1:0 | ||||
| 2. Round | 01/12/1965 | Chelsea FC | - | Wiener Sport-Club | 2:0 | ||||
| Round of 16 | 09/02/1966 | AC Milan | - | Chelsea FC | 2:1 | ||||
| Round of 16 | 16/02/1966 | Chelsea FC | - | AC Milan | 2:1 | ||||
| Round of 16 | 02/03/1966 | AC Milan | - | Chelsea FC | 1:1 aet | ||||
| Quarter-finals | 15/03/1966 | TSV 1860 München | - | Chelsea FC | 2:2 |  |
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| Quarter-finals | 29/03/1966 | Chelsea FC | - | TSV 1860 München | 1:0 | ||||
| Semi-finals | 27/04/1966 | FC Barcelona | - | Chelsea FC | 2:0 | ||||
| Semi-finals | 11/05/1966 | Chelsea FC | - | FC Barcelona | 2:0 | ||||
| Semi-finals | 25/05/1966 | FC Barcelona | - | Chelsea FC | 5:0 |
England