| Date | Location | Home | Away | Winner | By |
|---|---|---|---|---|---|
| 11/16/2018 | Willemstad | Aruba | Montserrat | Draw | 0.17 |
| 11/16/2018 | Bayamon | British Virgin Islands | Bonaire | British Virgin Islands | 1.80 |
| 11/16/2018 | Belmopan | Belize | Puerto Rico | Belize | 1.36 |
| 11/16/2018 | North Shore Village | Bermuda | El Salvador | El Salvador | 2.38 |
| 11/16/2018 | Saint George's | Grenada | Saint Martin | Grenada | 0.68 |
| 11/17/2018 | Managua | Nicaragua | Haiti | Haiti | 1.19 |
| 11/17/2018 | Montego Bay | Jamaica | Suriname | Jamaica | 1.07 |
| 11/17/2018 | Havana | Cuba | Dominican Republic | Draw | 0.21 |
| 11/17/2018 | George Town | Cayman Islands | St. Lucia | St. Lucia | 1.33 |
| 11/18/2018 | Nassau | Bahamas | Anguilla | Draw | 0.33 |
| 11/18/2018 | Basseterre | St. Kitts and Nevis | Canada | Canada | 1.12 |
| 11/18/2018 | Venetian Road Settlement | Turks and Caicos Islands | St. Vincent and Grenadines | St. Vincent and Grenadines | 3.31 |
| 11/18/2018 | Wildey | Barbados | US Virgin Islands | Barbados | 3.99 |
| 11/19/2018 | Willemstad | Curacao | Guadeloupe | Curacao | 3.22 |
| 11/19/2018 | Fort-de-France | Martinique | Antigua and Barbuda | Martinique | 1.22 |
| 11/20/2018 | Remire-Montjoly | French Guiana | Guyana | French Guiana | 1.37 |
| 11/20/2018 | The Valley | Sint Maarten | Dominica | Dominica | 3.95 |
| 3/21/2019 | Bayamon | British Virgin Islands | Turks and Caicos Islands | British Virgin Islands | 3.26 |
| 3/22/2019 | Arnos Vale | St. Vincent and Grenadines | Bonaire | St. Vincent and Grenadines | 2.96 |
| 3/22/2019 | George Town | Cayman Islands | Montserrat | Montserrat | 0.93 |
| 3/22/2019 | The Valley | Anguilla | US Virgin Islands | Anguilla | 2.06 |
| 3/23/2019 | San Salvador | El Salvador | Jamaica | El Salvador | 0.75 |
| 3/23/2019 | Les Abymes | Guadeloupe | Martinique | Martinique | 0.64 |
| 3/23/2019 | Paramaribo | Suriname | St. Kitts and Nevis | Suriname | 1.92 |
| 3/23/2019 | Leonora | Guyana | Belize | Draw | 0.04 |
| 3/24/2019 | San Cristobal | Dominican Republic | Bermuda | Dominican Republic | 1.85 |
| 3/24/2019 | Bayamon | Puerto Rico | Grenada | Puerto Rico | 0.70 |
| 3/24/2019 | Port-au-Prince | Haiti | Cuba | Haiti | 2.79 |
| 3/24/2019 | Wildey | Barbados | Nicaragua | Nicaragua | 0.62 |
| 3/25/2019 | The Valley | Sint Maarten | Saint Martin | Saint Martin | 2.98 |
| 3/25/2019 | North Sound | Antigua and Barbuda | Curacao | Curacao | 1.60 |
| 3/25/2019 | Gros Islet | St. Lucia | Aruba | St. Lucia | 1.12 |
| 3/26/2019 | Toronto | Canada | French Guiana | Canada | 2.08 |
| 3/26/2019 | Les Abymes | Dominica | Bahamas | Dominica | 2.48 |
