2nd Round
San Juan Jabloteh were seeded and received a bye to the 2nd round. San Juan Jabloteh and W Connection both hosted their first leg matchups on the same day and decided to host their matches as a billed doubleheader at Manny Ramjohn Stadium in Marabella. In Jabloteh's return leg to Suriname they were without head coach Terry Fenwick, who did not travel with the team because he had not been paid by the club since the end of the 2008 TT Pro League season.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| San Juan Jabloteh | 5 – 2 | Inter Moengotapoe | 2 – 1 | 3 – 1 |
| Hoppers | 0 – 8 | Tempête | 0 – 4 | 0 – 4 |
| W Connection | 4 – 1 | Cavaly | 3 – 1 | 1 – 0 |
Read more about this topic: 2009 CFU Club Championship