| 1. Round | 06/10/1965 | AS Roma | - | Chelsea FC | 0:0 | ||||
| 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 | ||||
| Semi-finals | 27/04/1966 | FC Barcelona | - | Chelsea FC | 2:0 | ||||
| Semi-finals | 25/05/1966 | FC Barcelona | - | Chelsea FC | 5:0 |
Scotland