North & Central America: CONCACAF Nations League - League C |
| Group C - 2. Round | Cayman Islands | Saint Kitts and Nevis | 1:4 (0:3, 1:1) | details | 07.09.2024 |
| Group C - 1. Round | British Virgin Islands | Cayman Islands | 0:1 (0:0, 0:1) | details | 04.09.2024 |
World: World Championship - Qualification - Second stage |
| Group A | Cuba | Cayman Islands | 3:0 AWA. | details | 11.06.2024 |
| Group A | Cayman Islands | Antigua and Barbuda | 1:0 (0:0, 1:0) | details | 08.06.2024 |
World: Friendly International - Main |
| | Moldova | Cayman Islands | 4:0 (2:0, 2:0) | details | 26.03.2024 |
North & Central America: CONCACAF Nations League - League C |
| Group B - 6. Round | Aruba | Cayman Islands | 5:1 (2:0, 3:1) | details | 20.11.2023 |
| Group B - 4. Round | Cayman Islands | United States Virgin Islands | 2:1 (1:0, 1:1) | details | 17.10.2023 |
| Group B - 2. Round | Cayman Islands | Aruba | 1:2 (1:1, 0:1) | details | 11.09.2023 |
| Group B - 1. Round | United States Virgin Islands | Cayman Islands | 2:2 (2:1, 0:1) | details | 08.09.2023 |
North & Central America: CONCACAF Nations League - League C |
| Group D - 6. Round | Puerto Rico | Cayman Islands | 5:1 (2:0, 3:1) | details | 27.03.2023 |
| Group D - 3. Round | Cayman Islands | Puerto Rico | 0:3 (0:1, 0:2) | details | 10.06.2022 |
| Group D - 2. Round | Cayman Islands | British Virgin Islands | 1:1 (1:0, 0:1) | details | 07.06.2022 |
| Group D - 1. Round | British Virgin Islands | Cayman Islands | 1:1 (0:0, 1:1) | details | 03.06.2022 |
World: World Championship - Qualification - First stage |
| Group B | Bermuda | Cayman Islands | 1:1 (0:1, 1:0) | details | 09.06.2021 |
| Group B | Cayman Islands | Aruba | 1:3 (1:2, 0:1) | details | 03.06.2021 |
| Group B | Cayman Islands | Canada | 0:11 (0:6, 0:5) | details | 30.03.2021 |
| Group B | Suriname | Cayman Islands | 3:0 (2:0, 1:0) | details | 24.03.2021 |
North & Central America: CONCACAF Nations League - League C |
| Group A - 6. Round | Barbados | Cayman Islands | 3:0 (1:0, 2:0) | details | 20.11.2019 |
| Group A - 5. Round | Cayman Islands | United States Virgin Islands | 1:0 (1:0, 0:0) | details | 17.11.2019 |
| Group A - 4. Round | Cayman Islands | Saint Martin | 1:0 (0:0, 1:0) | details | 16.10.2019 |
| Group A - 3. Round | Saint Martin | Cayman Islands | 3:0 (0:0, 3:0) | details | 12.10.2019 |
| Group A - 2. Round | Cayman Islands | Barbados | 3:2 (1:1, 2:1) | details | 09.09.2019 |
| Group A - 1. Round | United States Virgin Islands | Cayman Islands | 0:2 (0:0, 0:2) | details | 05.09.2019 |
North & Central America: CONCACAF Nations League - Qualification |
| 4. Round | Cayman Islands | Montserrat | 1:2 (0:1, 1:1) | details | 23.03.2019 |
| 3. Round | Cayman Islands | Saint Lucia | 0:0 (0:0, 0:0) | details | 18.11.2018 |
| 2. Round | Dominican Republic | Cayman Islands | 3:0 (2:0, 1:0) | details | 13.10.2018 |
| 1. Round | Jamaica | Cayman Islands | 4:0 (2:0, 2:0) | details | 10.09.2018 |
World: World Cup - Qualification - First stage |
| Final - 2nd leg | Cayman Islands | Belize | 1:1 (1:1, 0:0) | details | 30.03.2015 |
| Final - 1st leg | Belize | Cayman Islands | 0:0 (0:0, 0:0) | details | 26.03.2015 |
World: World Cup - Qualification - Second stage |
| Group A - 6. Round | Cayman Islands | Dominican Republic | 1:1 (0:1, 1:0) | details | 15.11.2011 |
| Group A - 5. Round | Dominican Republic | Cayman Islands | 4:0 (2:0, 2:0) | details | 11.11.2011 |
| Group A - 4. Round | El Salvador | Cayman Islands | 4:0 (3:0, 1:0) | details | 12.10.2011 |
| Group A - 3. Round | Cayman Islands | Suriname | 0:1 (0:0, 0:1) | details | 08.10.2011 |
| Group A - 2. Round | Cayman Islands | El Salvador | 1:4 (0:0, 1:4) | details | 07.09.2011 |
| Group A - 1. Round | Suriname | Cayman Islands | 1:0 (1:0, 0:0) | details | 02.09.2011 |
North & Central America: Caribbean Cup - Qualification - First stage |
| Group A | Puerto Rico | Cayman Islands | 2:0 | details | 07.10.2010 |
| Group A | Cayman Islands | Anguilla | 4:1 | details | 05.10.2010 |
| Group A | Saint Martin | Cayman Islands | 1:1 | details | 03.10.2010 |
North & Central America: Caribbean Cup - Qualification - Second stage |
| Group F | Grenada | Cayman Islands | 4:2 | details | 15.10.2008 |
| Group F | Cayman Islands | Martinique | 0:1 | details | 13.10.2008 |
| Group F | Guadeloupe | Cayman Islands | 7:1 | details | 11.10.2008 |
North & Central America: Caribbean Cup - Qualification - First stage |
| Group C | Cayman Islands | Bermuda | 0:0 | details | 31.08.2008 |
World: Friendly International - Main |
| | Cayman Islands | Bermuda | 0:0 (0:0, 0:0) | details | 31.08.2008 |
North & Central America: Caribbean Cup - Qualification - First stage |
| Group C | Cayman Islands | Antigua and Barbuda | 1:1 | details | 30.08.2008 |
World: Friendly International - Main |
| | Cayman Islands | Antigua and Barbuda | 1:1 | details | 29.08.2008 |
North & Central America: Caribbean Cup - Qualification - First stage |
| Group C | Cayman Islands | Saint Martin | 3:0 | details | 27.08.2008 |
World: Friendly International - Main |
| | Cayman Islands | Saint Martin | 3:0 | details | 27.08.2008 |
World: World Cup - Qualification - Preliminary |
| Semi-finals - 2nd leg - 1. Round | Cayman Islands | Bermuda | 1:3 | details | 31.03.2008 |
| Semi-finals - 1st leg - 1. Round | Bermuda | Cayman Islands | 1:1 | details | 03.02.2008 |
North & Central America: Caribbean Cup - Qualification - First stage |
| Group A | Cuba | Cayman Islands | 7:0 | details | 06.09.2006 |