Schedule
November, 2026
| Date | Match | Competition | ||||
| Sat, Nov 14 | Cayman Islands |  | v |  | Anguilla | Latin America and the Caribbean |
December, 2026
January, 2027
May, 2027
| Date | Match | Competition | ||||
| Thu, May 27 | Anguilla | | v |  | Montserrat | Latin America and the Caribbean |
July, 2027
August, 2027
| Date | Match | Competition | ||||
| Fri, Aug 6 | Antigua and Barbuda |  | v | | Anguilla | Latin America and the Caribbean |
October, 2027
| Date | Match | Competition | ||||
| Mon, Oct 4 | Anguilla | | v |  | US Virgin Islands | Latin America and the Caribbean |
February, 2028
| Date | Match | Competition | ||||
| Wed, Feb 2 | Anguilla | | v | | Antigua and Barbuda | Latin America and the Caribbean |
March, 2028
| Date | Match | Competition | ||||
| Sun, Mar 5 | Anguilla | | v |  | Guadeloupe | Latin America and the Caribbean |
| Mon, Mar 27 | Saint Kitts and Nevis |  | v | | Anguilla | Latin America and the Caribbean |
April, 2028
| Date | Match | Competition | ||||
| Sun, Apr 9 | US Virgin Islands | | v | | Anguilla | Latin America and the Caribbean |
November, 2028
| Date | Match | Competition | ||||
| Wed, Nov 29 | Saint Vincent and the Grenadines |  | v | | Anguilla | Latin America and the Caribbean |
December, 2028
January, 2029
| Date | Match | Competition | ||||
| Fri, Jan 5 | Anguilla | | v | | Saint Vincent and the Grenadines | Latin America and the Caribbean |
| Wed, Jan 17 | Anguilla | | v | | Cayman Islands | Latin America and the Caribbean |
February, 2029
| Date | Match | Competition | ||||
| Sun, Feb 4 | Bonaire |  | v | | Anguilla | Latin America and the Caribbean |
| Sat, Feb 17 | Turks and Caicos Islands |  | v | | Anguilla | Latin America and the Caribbean |
May, 2029
| Date | Match | Competition | ||||
| Thu, May 31 | Montserrat | | v | | Anguilla | Latin America and the Caribbean |
August, 2029
| Date | Match | Competition | ||||
| Thu, Aug 2 | Anguilla | | v |  | Sint Maarten | Latin America and the Caribbean |
October, 2029
| Date | Match | Competition | ||||
| Fri, Oct 26 | Anguilla | | v | | Saint Kitts and Nevis | Latin America and the Caribbean |
November, 2029
December, 2029
| Date | Match | Competition | ||||
| Sun, Dec 30 | Anguilla | | v | | Turks and Caicos Islands | Latin America and the Caribbean |
January, 2030
| Date | Match | Competition | ||||
| Sat, Jan 19 | British Virgin Islands |  | v | | Anguilla | Latin America and the Caribbean |
| Sun, Jan 27 | Anguilla | | v | | British Virgin Islands | Latin America and the Caribbean |
February, 2030
| Date | Match | Competition | ||||
| Wed, Feb 27 | Saint Lucia |  | v | | Anguilla | Latin America and the Caribbean |
April, 2030
| Date | Match | Competition | ||||
| Wed, Apr 3 | Anguilla | | v |  | Curacao | Latin America and the Caribbean |
| Wed, Apr 17 | Martinique |  | v | | Anguilla | Latin America and the Caribbean |
| Mon, Apr 29 | Guadeloupe | | v | | Anguilla | Latin America and the Caribbean |
May, 2030
| Date | Match | Competition | ||||
| Fri, May 3 | Anguilla | | v | | Martinique | Latin America and the Caribbean |
| Sat, May 4 | Sint Maarten | | v | | Anguilla | Latin America and the Caribbean |
SMT