| Date | Location | Home | Away | Winner | By |
|---|---|---|---|---|---|
| 3/21/2019 | TBD | British Virgin Islands | Turks and Caicos Islands | British Virgin Islands | 2.15 |
| 3/22/2019 | Arnos Vale | St. Vincent and Grenadines | Bonaire | St. Vincent and Grenadines | 2.73 |
| 3/22/2019 | George Town | Cayman Islands | Montserrat | Montserrat | 0.89 |
| 3/22/2019 | The Valley | Anguilla | US Virgin Islands | Anguilla | 1.74 |
| 3/23/2019 | San Salvador | El Salvador | Jamaica | El Salvador | 0.63 |
| 3/23/2019 | Les Abymes | Guadeloupe | Martinique | Martinique | 0.53 |
| 3/23/2019 | Paramaribo | Suriname | St. Kitts and Nevis | Suriname | 2.01 |
| 3/23/2019 | Leonora | Guyana | Belize | Draw | 0.03 |
| 3/24/2019 | Port-au-Prince | Haiti | Cuba | Haiti | 2.67 |
| 3/24/2019 | Bayamón | Puerto Rico | Grenada | Puerto Rico | 0.65 |
| 3/24/2019 | Wildey | Barbados | Nicaragua | Draw | 0.49 |
| 3/24/2019 | San Cristóbal | Dominican Republic | Bermuda | Dominican Republic | 1.57 |
| 3/25/2019 | The Valley | Sint Maarten | Saint Martin | Saint Martin | 2.17 |
| 3/25/2019 | North Sound | Antigua and Barbuda | Curacao | Curacao | 1.61 |
| 3/25/2019 | Gros Islet | St. Lucia | Aruba | St. Lucia | 1.07 |
| 3/26/2019 | TBD | British Virgin Islands | Bonaire | British Virgin Islands | 1.79 |
| 3/26/2019 | Toronto | Canada | French Guiana | Canada | 2.09 |
| 3/26/2019 | Les Abymes | Dominica | Bahamas | Dominica | 2.25 |
