Schedule
August, 2026
| Date | Match | Competition | ||||
| Thu, Aug 27 | British Virgin Islands |  | v |  | Cayman Islands | Latin America and the Caribbean |
October, 2026
| Date | Match | Competition | ||||
| Thu, Oct 15 | Cayman Islands | | v |  | Turks and Caicos Islands | Latin America and the Caribbean |
| Fri, Oct 16 | Turks and Caicos Islands | | v | | Cayman Islands | Latin America and the Caribbean |
November, 2026
| Date | Match | Competition | ||||
| Sat, Nov 7 | Cayman Islands | | v |  | Saint Martin | Latin America and the Caribbean |
| Sat, Nov 14 | Cayman Islands | | v |  | Anguilla | Latin America and the Caribbean |
| Fri, Nov 27 | US Virgin Islands |  | v | | Cayman Islands | Latin America and the Caribbean |
December, 2026
| Date | Match | Competition | ||||
| Thu, Dec 24 | Curacao |  | v | | Cayman Islands | Latin America and the Caribbean |
January, 2027
| Date | Match | Competition | ||||
| Sat, Jan 9 | Cayman Islands | | v |  | Saint Kitts and Nevis | Latin America and the Caribbean |
| Tue, Jan 12 | Antigua and Barbuda |  | v | | Cayman Islands | Latin America and the Caribbean |
| Sat, Jan 30 | Saint Lucia |  | v | | Cayman Islands | Latin America and the Caribbean |
February, 2027
| Date | Match | Competition | ||||
| Tue, Feb 2 | Montserrat |  | v | | Cayman Islands | Latin America and the Caribbean |
| Sun, Feb 28 | Cayman Islands | | v |  | Guadeloupe | Latin America and the Caribbean |
March, 2027
| Date | Match | Competition | ||||
| Sat, Mar 13 | Martinique |  | v | | Cayman Islands | Latin America and the Caribbean |
| Tue, Mar 23 | Saint Kitts and Nevis | | v | | Cayman Islands | Latin America and the Caribbean |
| Mon, Mar 29 | Saint Vincent and the Grenadines |  | v | | Cayman Islands | Latin America and the Caribbean |
May, 2027
| Date | Match | Competition | ||||
| Sun, May 9 | Cayman Islands | | v |  | Dominica | Latin America and the Caribbean |
| Sun, May 16 | Dominica | | v | | Cayman Islands | Latin America and the Caribbean |
July, 2027
| Date | Match | Competition | ||||
| Sat, Jul 3 | Saint Martin | | v | | Cayman Islands | Latin America and the Caribbean |
| Thu, Jul 15 | Cayman Islands | | v | | Montserrat | Latin America and the Caribbean |
October, 2027
| Date | Match | Competition | ||||
| Sat, Oct 30 | Cayman Islands | | v | | British Virgin Islands | Latin America and the Caribbean |
March, 2028
| Date | Match | Competition | ||||
| Thu, Mar 30 | Cayman Islands | | v | | Saint Lucia | Latin America and the Caribbean |
| Fri, Mar 31 | Guadeloupe | | v | | Cayman Islands | Latin America and the Caribbean |
May, 2028
| Date | Match | Competition | ||||
| Thu, May 11 | Cayman Islands | | v |  | Bonaire | Latin America and the Caribbean |
August, 2028
| Date | Match | Competition | ||||
| Tue, Aug 22 | Cayman Islands | | v | | Curacao | Latin America and the Caribbean |
January, 2029
| Date | Match | Competition | ||||
| Wed, Jan 17 | Anguilla | | v | | Cayman Islands | Latin America and the Caribbean |
February, 2029
| Date | Match | Competition | ||||
| Sun, Feb 11 | Bonaire | | v | | Cayman Islands | Latin America and the Caribbean |
| Sun, Feb 18 | Cayman Islands | | v | | US Virgin Islands | Latin America and the Caribbean |
March, 2029
| Date | Match | Competition | ||||
| Fri, Mar 9 | Sint Maarten |  | v | | Cayman Islands | Latin America and the Caribbean |
October, 2029
| Date | Match | Competition | ||||
| Tue, Oct 2 | Cayman Islands | | v |  | Aruba | Latin America and the Caribbean |
November, 2029
| Date | Match | Competition | ||||
| Wed, Nov 21 | Cayman Islands | | v | | Sint Maarten | Latin America and the Caribbean |
March, 2030
| Date | Match | Competition | ||||
| Wed, Mar 13 | Aruba | | v | | Cayman Islands | Latin America and the Caribbean |
April, 2030
| Date | Match | Competition | ||||
| Fri, Apr 19 | Cayman Islands | | v | | Saint Vincent and the Grenadines | Latin America and the Caribbean |
May, 2030
| Date | Match | Competition | ||||
| Thu, May 9 | Cayman Islands | | v | | Martinique | Latin America and the Caribbean |