1st Round
The first round was contested in five two-legged matchups. Team #1 in each matchup hosted the first leg. The schedule for the first round legs was updated on March 11 due to necessary travel accommodations for clubs and local events occurring in Aruba and Haiti that would conflict with the original match schedule.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Sevilla FC Puerto Rico | 3 – 5 | Hoppers | 3 – 3 | 0 – 2 |
| Centre Bath Estate | 1 – 17 | W Connection | 0 – 5 | 1 – 12 |
| Alpha United FC | 1 – 3 | Tempête | 1 – 1 | 0 – 2 |
| Cavaly | 6 – 0 | Britannia | 5 – 0 | 1 – 0 |
| CSD Barber | 2 – 3 | Inter Moengotapoe | 1 – 3 | 1 – 0 |
Read more about this topic: 2009 CFU Club Championship