| 2. Round | 15/07/2009 | Inter Turku | - | FC Sheriff | 0:1 |  |
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| 2. Round | 21/07/2009 | FC Sheriff | - | Inter Turku | 1:0 | |
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| 3. Round | 29/07/2009 | FC Sheriff | - | Slavia Praha | 0:0 | ||||
| 3. Round | 05/08/2009 | Slavia Praha | - | FC Sheriff | 1:1 | ||||
| Play-offs | 18/08/2009 | FC Sheriff | - | Olympiakos Piraeus | 0:2 | ||||
| Play-offs | 26/08/2009 | Olympiakos Piraeus | - | FC Sheriff | 1:0 |
Moldova
Russia