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This is a list of the Cayman Islands national football team results.
| 7 October 2008 Friendly | Cayman Islands | 2–0 | Stultz Academy | Miami, United States |
| Stadium: Cypress Sports Ground |
| 24 March 1990 Caribbean Cup | Sint Maarten | 1–1 |
| 28 March 1990 Caribbean Cup | Cayman Islands | 2–1 |
| 30 March 1990 Caribbean Cup | Saint Martin | 1–5 |
| 1 April 1990 Caribbean Cup | Saint Martin | 2–3 |
| 26 May 1991 Caribbean Cup | Jamaica | 3–2 | ||
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| 28 May 1991 Caribbean Cup | Guyana | 2–1 | ||
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| 11 March 1993 Caribbean Cup | Guyana | 3–2 | ||
| 12 March 1993 Caribbean Cup | Barbados | 6–1 | ||
| 14 March 1993 Caribbean Cup | Puerto Rico | 4–0 | ||
| 12 May 1998 World Cup qualification | Cayman Islands | 0–1 | George Town, Cayman Islands | |
| Report |
| Stadium: Truman Bodden Attendance: 2,000 Referee: Argelio Sabillon (Honduras) |
| 14 May 1998 World Cup qualification | Cuba | 5–0 | George Town, Cayman Islands | |
| Report |
| Stadium: Truman Bodden Attendance: 1,200 Referee: Pascual Rebolledo Cárdenas (Mexico) |
| 5 March 2002 World Cup qualification | Cuba | 4–0 | Havana | |
| Report | Stadium: Estadio Pedro Marrero Attendance: 11,000 Referee: Argelio Sabillon Hughil Thompson (Jamaica) |
| 19 March 2002 World Cup qualification | Cayman Islands | 0–0 | George Town, Cayman Islands | |
| Report | Stadium: Truman Bodden Attendance: 5,000 Referee: Ibrahim Brohim (Dominica) |
| 3 February 2006 World Cup qualification | Cayman Islands | 1–2 | George Town, Cayman Islands | |
| Report | Stadium: Truman Bodden Stadium Attendance: 1,789 Referee: Rodolfo Sibrian (El Salvador) |
| 27 March 2006 World Cup qualification | Cuba | 3–0 | Havana, Cuba | |
| Report | Stadium: Estadio Pedro Marrero Attendance: 3,500 Referee: Marco Rodriguez (Mexico) |
| 3 February 2010 World Cup qualification | Bermuda | 1–1 | Hamilton, Bermuda | |
| Report |
| Stadium: Bermuda National Stadium Attendance: 2,000 Referee: Mauricio Navarro (Canada) |
| 30 March 2010 World Cup qualification | Cayman Islands | 1–3 | George Town, Cayman Islands | |
| Report | Stadium: Truman Bodden Stadium Attendance: 3,200 Referee: Jair Marrufo (United States) |
| 27 August 2008 Caribbean Cup qualification | Cayman Islands | 3–0 | George Town, Cayman Islands | |
| Report | Stadium: Truman Bodden Stadium Attendance: 300 Referee: Kevin Thomas (Jamaica) |
| 30 August 2008 Caribbean Cup qualification | Cayman Islands | 1–1 | George Town, Cayman Islands | |
| Report |
| Stadium: Truman Bodden Stadium Attendance: 350 Referee: Jeoffrey Hospadalis (Trinidad and Tobago) |
| 31 August 2008 Caribbean Cup qualification | Cayman Islands | 0–0 | George Town, Cayman Islands | |
| Report | Stadium: Truman Bodden Stadium Attendance: 350 Referee: Geoffrey Hospedales (Trinidad and Tobago) |
| 7 October Friendly | Cayman Islands | 1–0 | Miami, United States | |
| Stadium: Cypress Sports Ground |
| 11 October 2008 Caribbean Cup qualification | Guadeloupe | 7–1 | Les Abymes, Guadeloupe | |
| Report |
| Stadium: Stade René Serge Nabajoth Attendance: 4,200 Referee: Roy McArthur (Grenada) |
| 13 October 2008 Caribbean Cup qualification | Cayman Islands | 0–1 | Les Abymes, Guadeloupe | |
| Report |
| Stadium: Stade René Serge Nabajoth Attendance: 1,000 Referee: James Matthew (Saint Kitts and Nevis) |
| 15 October 2008 Caribbean Cup qualification | Grenada | 4–2 | Les Abymes, Guadeloupe | |
| Report |
| Stadium: Stade René Serge Nabajoth Attendance: 3,358 Referee: Bryan Willett (Antigua and Barbuda) |
| 5 November Friendly | Cayman Islands | 1–6 | George Town, Cayman Islands | |
| Stadium: Truman Bodden Stadium |
| 9 November Friendly | Cayman Islands | 0–2 | George Town, Cayman Islands | |
| Stadium: Truman Bodden Stadium |
| 2 September 2014 World Cup qualification | Suriname | 1–0 | Paramaribo | |
| Report | Stadium: André Kamperveen Stadion Attendance: 1,000 Referee: Adrian Skeete (Barbados) |
| 6 September 2014 World Cup qualification | Cayman Islands | 1–4 | George Town | |
| M. Ebanks | Report | Bautista Anaya García | Stadium: Truman Bodden Stadium Attendance: 2,200 Referee: Elmar Rodas (Guatemala) |
| 7 October 2014 World Cup qualification | Cayman Islands | 0–1 | George Town | |
| Report | Drenthe | Stadium: Truman Bodden Stadium Attendance: 2,100 Referee: Edvin Jurisevic (United States) |
| 11 October 2014 World Cup qualification | El Salvador | 4–0 | San Salvador | |
| Turcios Purdy J. Alas Sosa | Report | Stadium: Estadio Cuscatlán Attendance: 17,570 Referee: Hugo Cruz (Costa Rica) |
| 11 November 2014 World Cup qualification | Dominican Republic | 4–0 | San Cristóbal | |
| Navarro Ozuna Rodríguez Morillo | Report | Stadium: Estadio Panamericano Attendance: 1,000 Referee: José Guerrero (Nicaragua) |
| 14 November 2014 World Cup qualification | Cayman Islands | 1–1 | George Town | |
| M. Ebanks | Report | García | Stadium: Truman Bodden Stadium Attendance: 1,750 Referee: James Matthew (Saint Kitts and Nevis) |
| 25 March 2018 World Cup qualification | Belize | 0–0 | Belmopan | |
| Stadium: FFB Stadium Attendance: 1,924 Referee: Oscar Reyna (Guatemala) |
| 29 March 2018 World Cup qualification | Cayman Islands | 1–1 | George Town | |
| Report |
| Stadium: Truman Bodden Sports Complex Attendance: 1,800 Referee: Yadel Martínez (Cuba) |
| 5 September 2019-20 CONCACAF Nations League | U.S. Virgin Islands | 0–2 | Upper Bethlehem | |
| Report |
| Stadium: Bethlehem Soccer Stadium Referee: Tristley Bassue (Saint Kitts and Nevis) |
| 8 September 2019-20 CONCACAF Nations League | Cayman Islands | 3–2 | George Town | |
| Report | Stadium: Truman Bodden Sports Complex Referee: Luis Enrique Santander (Mexico) |
| 12 October 2019-20 CONCACAF Nations League | Saint Martin | 3–0 | The Valley | |
| Report | Stadium: Raymond E. Guishard Technical Centre Referee: Oshane Nation (Jamaica) |
| 15 October 2019-20 CONCACAF Nations League | Cayman Islands | 1–0 | George Town | |
| Report | Stadium: Truman Bodden Sports Complex Referee: Fernando Hernández (Mexico) |
| 16 November 2019-20 CONCACAF Nations League | Cayman Islands | 1–0 | George Town | |
| Report | Stadium: Truman Bodden Sports Complex Referee: José Kellys (Panama) |
| 19 November 2019-20 CONCACAF Nations League | Barbados | 3–0 | Bridgetown | |
| Report | Stadium: Wildey Turf Referee: Kimbell Ward (Saint Kitts and Nevis) |
| 24 March 2022 World Cup qualification | Suriname | 3–0 | Paramaribo, Suriname | |
| 19:00 UTC−3 |
| Report | Stadium: Dr. Ir. Franklin Essed Stadion Referee: Jorge Pérez (Mexico) |
| 29 March 2022 World Cup qualification | Cayman Islands | 0–11 | Bradenton, United States | |
| 18:00 UTC−4 | Report | Stadium: IMG Academy Referee: Ted Unkel (United States) |
| 2 June 2022 World Cup qualification | Cayman Islands | 1–3 | Bradenton, United States | |
| 18:00 UTC−4 | Report |
| Stadium: IMG Academy Referee: Luis Enrique Santander (Mexico) |
| 8 June 2022 World Cup qualification | Bermuda | 1–1 | Bradenton, United States | |
| 20:00 UTC−4 |
| Report |
| Stadium: IMG Academy Referee: Rubiel Vazquez (United States) |
| 3 June 2022–23 Nations League | British Virgin Islands | 1–1 | Road Town, British Virgin Islands | |
| 16:00 UTC−4 |
| Report |
| Stadium: A. O. Shirley Recreation Ground Referee: Nima Saghafi (United States) |
| 6 June 2022–23 Nations League | Cayman Islands | 1–1 | George Town, Cayman Islands | |
| 18:00 UTC−5 | J. Ebanks | Report | Wilson | Stadium: Truman Bodden Sports Complex Referee: Rubiel Vazquez (United States) |
| 9 June 2022–23 Nations League | Cayman Islands | 0–3 | George Town, Cayman Islands | |
| 18:00 UTC−5 | Report | Stadium: Truman Bodden Sports Complex Referee: Sergio Reyna (Guatemala) |
| 26 March 2022–23 Nations League | Puerto Rico | 5–1 | Bayamón, Puerto Rico | |
| 18:00 UTC−4 | Report |
| Stadium: Estadio Juan Ramón Loubriel Referee: Ekaterina Koroleva (United States) |
| 7 September 2023–24 Nations League | U.S. Virgin Islands | 2–2 | Saint Croix, U.S. Virgin Islands | |
| 19:00 UTC−4 |
| Report |
| Stadium: Bethlehem Soccer Stadium Referee: Reon Radix (Grenada) |
| 11 September 2023–24 Nations League | Cayman Islands | 1–2 | George Town, Cayman Islands | |
| 15:30 UTC−5 |
| Report | Stadium: Truman Bodden Sports Complex Referee: Ismael Cornejo (El Salvador) |
| 17 October 2023–24 Nations League | Cayman Islands | 2–1 | George Town, Cayman Islands | |
| 15:30 UTC−5 | Report |
| Stadium: Truman Bodden Sports Complex Referee: Randy Encarnación (Dominican Republic) |
| 20 November 2023–24 Nations League | Aruba | 5–1 | Oranjestad, Aruba | |
| 15:00 UTC−4 |
| Report |
| Stadium: Trinidad Stadium Referee: Norberto da Silva (Curaçao) |
| 26 March Friendly | Cayman Islands | 0–4 | Antalya, Turkey | |
| 17:00 UTC+3 | Report | Stadium: Mardan Sports Complex |
| 8 June 2026 FIFA World Cup qualification | Cayman Islands | 1–0 | George Town, Cayman Islands | |
| 21:00 UTC−5 |
| Report (FIFA) Report (CONCACAF) | Stadium: Truman Bodden Sports Complex Attendance: 453 Referee: Pierre-Luc Lauzière (Canada) |
| 11 June 2026 FIFA World Cup qualification | Cuba | 3–0 Awarded [note 1] | Santiago de Cuba, Cuba | |
| 15:30 UTC−4 | Report (FIFA) Report (CONCACAF) | Stadium: Estadio Antonio Maceo |
| 4 September 2024–25 Nations League | British Virgin Islands | 0–1 | George Town, Cayman Islands | |
| 16:30 (15:30 UTC−5) | Report | Seymour | Referee: Jonathan Leiton (Costa Rica) |
| 7 September 2024–25 Nations League | Cayman Islands | 1–4 | George Town, Cayman Islands | |
| 16:30 (15:30 UTC−5) | Duval | Report | Referee: Moeth Gaymes (Saint Vincent and the Grenadines) |
| 12 October 2024–25 Nations League | Cayman Islands | 1–0 | Basseterre, Saint Kitts and Nevis | |
| 15:30 | Douglas | Report | Attendance: 100 [1] Referee: Ricangel De Leça (Aruba) |
| 15 October 2024–25 Nations League | Saint Kitts and Nevis | 1–1 | Basseterre, Saint Kitts and Nevis | |
| 15:30 | Campbell | Report | Scott | Referee: Shekiel Jokil (Suriname) |
| 15 November 2024–25 Nations League | Cayman Islands | 0–6 | George Town, Cayman Islands | |
| 15:00 | Report | Attendance: 194 [2] Referee: Adonai Escobedo (Mexico) |
| 19 November 2024–25 Nations League | Guadeloupe | 1–0 | Le Gosier, Guadeloupe | |
| 17:00 (18:00 UTC−4) |
| Report | Referee: Ismael Cornejo (El Salvador) |
| 4 June 2026 FIFA World Cup qualification | Bermuda | 5–0 | Devonshire Parish, Bermuda | |
| 20:00 UTC−3 | Report | Stadium: Bermuda National Stadium Referee: Rubiel Vazquez (United States) |
| 7 June 2026 FIFA World Cup qualification | Cayman Islands | 0–1 | George Town, Cayman Islands | |
| 15:00 UTC−5 | Report | Robinson | Stadium: Truman Bodden Sports Complex Referee: Adonis Carrasco (Dominican Republic) |