UEFA Cup 2008/09, First Round, 2nd leg
| Vitoria Guimaraes (Portugal) |
2:2 (2:0) aet |
Portsmouth FC (England) |
| Stadium: | ||
| Match time, city: | 2 October 2008, Guimaraes | |
| Referee: | Selcuk Dereli (Turkey) | |
| Goals | ||
Douglas  19' | 1:0 | |
Joao Alves  31' | 2:0 | |
| 2:1 | 105'  Crouch | |
| 2:2 | 111' Crouch | |
| First leg: 0:2 (aggregate 2:4) | ||
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