| Match | Date | Venue | Team A | Score | Team B |
| 1 | March 10th - 20:00 | BAA Field, Pembroke, Bermuda | Dandytown (BER) | 1-1 | Defence Force (TRI) |
| 2 | March 10th -20:00 | Warner Park - St. Kitts & Nevis | Newtown United FC (SKN) | 0-1 | Caledonia AIA (TRI) |
| 3 | March 13rd - 16:00 | Mindoo Phillip Park, St. Lucia | Northern United All Stars (SLU) | 0-3 | S.V. Walking Boyz Co. (SUR) |
| 4 | March 13th - 19:30 | MacKensie Sports Club Ground - Linden, Guyana | Milerock FC (GUY) | 0-1 | Intermoengotapoe S.V. (SUR) |
| 5 | March 18th - 19:00 | T.E. Mcfield Annex Sports Centre - Cayman Islands | River Plate FC (PUR) | 2-0 | Bodden Town FC (CAY) |
| Match | Date | Venue | Team A | Score | Team B |
| 6 | March 19th - 18:00 | Mannie Ramjohn Stadium -Trinidad & Tobago | Defence Force (TRI) | 0-0 | Dandytown (BER) |
| 7 | March 19th -19:30 | Hasely Crawford Stadium - Trinidad & Tobago | Caledonia AIA (TRI) | 5-0 | Newtown United FC (SKN) |
| 8 | March 20th - 19:00 | T.E. Mcfield Annex Sports Centre - Cayman Islands | Bodden Town FC (CAY) | 1-0 | River Plate FC (PUR) |
| 9 | March 26th - 19:00 | Andre Kamperveen Stadium, Paramaribo | S.V. Walking Boyz Co. (SUR) | 3-1 | Northern United All Stars (SLU) |
| 10 | March 19th - 19:00 | Andre Kamperveen Stadium, Paramaribo | Intermoengotapoe S.V. (SUR) | 1-2 | Milerock FC (GUY) |
CFU Club Championship Cup - Round 1