Schedule
August, 2026
| Date | Match | Competition | ||||
| Fri, Aug 21 | Montserrat |  | v |  | Saint Vincent and the Grenadines | Latin America and the Caribbean |
September, 2026
| Date | Match | Competition | ||||
| Wed, Sep 2 | Montserrat | | v |  | US Virgin Islands | Latin America and the Caribbean |
| Sat, Sep 19 | Saint Martin |  | v | | Montserrat | Latin America and the Caribbean |
October, 2026
| Date | Match | Competition | ||||
| Sun, Oct 25 | Montserrat | | v |  | Sint Maarten | Latin America and the Caribbean |
November, 2026
| Date | Match | Competition | ||||
| Mon, Nov 9 | Montserrat | | v |  | Guadeloupe | Latin America and the Caribbean |
| Tue, Nov 17 | Montserrat | | v |  | Dominica | Latin America and the Caribbean |
January, 2027
| Date | Match | Competition | ||||
| Fri, Jan 22 | Saint Vincent and the Grenadines | | v | | Montserrat | Latin America and the Caribbean |
| Sun, Jan 24 | Montserrat | | v |  | Turks and Caicos Islands | Latin America and the Caribbean |
| Tue, Jan 26 | Dominica | | v | | Montserrat | Latin America and the Caribbean |
February, 2027
| Date | Match | Competition | ||||
| Mon, Feb 1 | Saint Lucia |  | v | | Montserrat | Latin America and the Caribbean |
| Tue, Feb 2 | Montserrat | | v |  | Cayman Islands | Latin America and the Caribbean |
| Wed, Feb 3 | Saint Kitts and Nevis |  | v | | Montserrat | Latin America and the Caribbean |
May, 2027
| Date | Match | Competition | ||||
| Fri, May 14 | Bonaire |  | v | | Montserrat | Latin America and the Caribbean |
| Thu, May 27 | Anguilla |  | v | | Montserrat | Latin America and the Caribbean |
July, 2027
| Date | Match | Competition | ||||
| Fri, Jul 2 | US Virgin Islands | | v | | Montserrat | Latin America and the Caribbean |
| Thu, Jul 15 | Cayman Islands | | v | | Montserrat | Latin America and the Caribbean |
August, 2027
| Date | Match | Competition | ||||
| Mon, Aug 9 | Antigua and Barbuda |  | v | | Montserrat | Latin America and the Caribbean |
| Wed, Aug 11 | Montserrat | | v |  | Martinique | Latin America and the Caribbean |
November, 2027
| Date | Match | Competition | ||||
| Fri, Nov 12 | Guadeloupe | | v | | Montserrat | Latin America and the Caribbean |
December, 2027
| Date | Match | Competition | ||||
| Thu, Dec 9 | Montserrat | | v |  | Curacao | Latin America and the Caribbean |
April, 2028
| Date | Match | Competition | ||||
| Sat, Apr 15 | Martinique | | v | | Montserrat | Latin America and the Caribbean |
June, 2028
| Date | Match | Competition | ||||
| Mon, Jun 5 | Montserrat | | v |  | British Virgin Islands | Latin America and the Caribbean |
| Mon, Jun 26 | Montserrat | | v |  | Aruba | Latin America and the Caribbean |
September, 2028
| Date | Match | Competition | ||||
| Sat, Sep 2 | Sint Maarten | | v | | Montserrat | Latin America and the Caribbean |
November, 2028
| Date | Match | Competition | ||||
| Sat, Nov 25 | Montserrat | | v | | Saint Lucia | Latin America and the Caribbean |
December, 2028
| Date | Match | Competition | ||||
| Wed, Dec 6 | Aruba | | v | | Montserrat | Latin America and the Caribbean |
May, 2029
| Date | Match | Competition | ||||
| Wed, May 23 | Curacao | | v | | Montserrat | Latin America and the Caribbean |
| Thu, May 31 | Montserrat | | v | | Anguilla | Latin America and the Caribbean |
June, 2029
| Date | Match | Competition | ||||
| Fri, Jun 1 | British Virgin Islands | | v | | Montserrat | Latin America and the Caribbean |
| Fri, Jun 29 | Montserrat | | v | | Antigua and Barbuda | Latin America and the Caribbean |
July, 2029
| Date | Match | Competition | ||||
| Tue, Jul 10 | Montserrat | | v | | Saint Martin | Latin America and the Caribbean |
September, 2029
| Date | Match | Competition | ||||
| Tue, Sep 11 | Montserrat | | v | | Saint Kitts and Nevis | Latin America and the Caribbean |
| Wed, Sep 19 | Turks and Caicos Islands | | v | | Montserrat | Latin America and the Caribbean |
February, 2030
| Date | Match | Competition | ||||
| Thu, Feb 7 | Montserrat | | v | | Bonaire | Latin America and the Caribbean |