series
| Sept. 29, 2008 | TRI1 | 2008 | 23 | St Ann's Rangers | 2 - 1 | Tobago United | 1 | |
| July 15, 2008 | TRI1 | 2008 | 13 | St Ann's Rangers | 2 - 0 | Tobago United | 1 | |
| May 3, 2008 | TRI1 | 2008 | 5 | St Ann's Rangers | 5 - 1 | Tobago United | 1 |
scoreboard
| BEL1 | 2008-2009 | 6 | Dender EH | 1 - 4 | KV Mechelen | 1 | |
| POR1 | 2008-2009 | 4 | C.F. Os Belenenses | 0 - 1 | Leixões | 1 |