| 2026-03-29 |  British Virgin Islandsv AnguillaCONCACAF Series | 4–0 | CONCACAF Series |
| 2026-03-26 |  BahamasvAnguillaCONCACAF Series | 1–3 | CONCACAF Series |
| 2025-11-15 |  Cayman IslandsvAnguillaCONCACAF Series | 4–0 | CONCACAF Series |
| 2025-11-12 | BahamasvAnguillaCONCACAF Series | 1–2 | CONCACAF Series |
| 2025-06-07 | Anguillav El SalvadorFIFA World Cup qualification | 0–3 | FIFA World Cup qualification |
| 2025-06-04 |  Saint Vincent and the GrenadinesvAnguillaFIFA World Cup qualification | 6–0 | FIFA World Cup qualification |
| 2025-06-01 |  GrenadavAnguillaFriendly | 2–0 | Friendly |
| 2025-05-25 | Anguillav Saint Kitts and NevisFriendly | 2–4 | Friendly |
| 2024-10-12 |  Turks and Caicos IslandsvAnguillaCONCACAF Nations League | 2–1 | CONCACAF Nations League |
| 2024-10-09 |  BelizevAnguillaCONCACAF Nations League | 1–0 | CONCACAF Nations League |
| 2024-09-10 | BelizevAnguillaCONCACAF Nations League | 1–0 | CONCACAF Nations League |
| 2024-09-04 | Turks and Caicos IslandsvAnguillaCONCACAF Nations League | 0–2 | CONCACAF Nations League |
| 2024-06-11 |  Puerto RicovAnguillaFIFA World Cup qualification | 8–0 | FIFA World Cup qualification |
| 2024-06-08 | Anguillav SurinameFIFA World Cup qualification | 0–4 | FIFA World Cup qualification |
| 2024-03-26 | Turks and Caicos IslandsvAnguillaFIFA World Cup qualification | 1–1 p | FIFA World Cup qualification |
| 2024-03-22 | AnguillavTurks and Caicos IslandsFIFA World Cup qualification | 0–0 | FIFA World Cup qualification |
| 2023-11-18 | Anguillav BonaireCONCACAF Nations League | 0–3 | CONCACAF Nations League |
| 2023-10-16 |  Saint MartinvAnguillaCONCACAF Nations League | 8–0 | CONCACAF Nations League |
| 2023-10-12 | BonairevAnguillaCONCACAF Nations League | 2–0 | CONCACAF Nations League |
| 2023-09-07 | AnguillavSaint MartinCONCACAF Nations League | 0–6 | CONCACAF Nations League |
| 2023-03-24 | Anguillav Saint LuciaCONCACAF Nations League | 1–2 | CONCACAF Nations League |
| 2022-06-12 | Saint LuciavAnguillaCONCACAF Nations League | 2–0 | CONCACAF Nations League |
| 2022-06-05 |  DominicavAnguillaCONCACAF Nations League | 1–1 | CONCACAF Nations League |
| 2022-06-02 | AnguillavDominicaCONCACAF Nations League | 0–0 | CONCACAF Nations League |
| 2021-06-05 |  PanamavAnguillaFIFA World Cup qualification | 13–0 | FIFA World Cup qualification |
| 2021-06-02 | DominicavAnguillaFIFA World Cup qualification | 3–0 | FIFA World Cup qualification |
| 2021-03-30 |  BarbadosvAnguillaFIFA World Cup qualification | 1–0 | FIFA World Cup qualification |
| 2021-03-27 | Anguillav Dominican RepublicFIFA World Cup qualification | 0–6 | FIFA World Cup qualification |
| 2019-11-19 | Puerto RicovAnguillaCONCACAF Nations League | 3–0 | CONCACAF Nations League |
| 2019-11-10 |  Trinidad and TobagovAnguillaFriendly | 15–0 | Friendly |
| 2019-10-15 | AnguillavPuerto RicoCONCACAF Nations League | 2–3 | CONCACAF Nations League |
| 2019-10-12 | Anguillav GuatemalaCONCACAF Nations League | 0–5 | CONCACAF Nations League |
| 2019-09-05 | GuatemalavAnguillaCONCACAF Nations League | 10–0 | CONCACAF Nations League |
| 2019-03-22 | Anguillav United States Virgin IslandsCONCACAF Nations League qualification | 0–3 | CONCACAF Nations League qualification |
| 2018-11-18 | BahamasvAnguillaCONCACAF Nations League qualification | 1–1 | CONCACAF Nations League qualification |
| 2018-10-14 |  NicaraguavAnguillaCONCACAF Nations League qualification | 6–0 | CONCACAF Nations League qualification |
| 2018-09-07 | Anguillav French GuianaCONCACAF Nations League qualification | 0–5 | CONCACAF Nations League qualification |
| 2018-08-25 | AnguillavSaint MartinFriendly | 1–2 | Friendly |
| 2018-08-22 |  Sint MaartenvAnguillaFriendly | 1–1 | Friendly |
| 2018-07-27 |  Saint BarthélemyvAnguillaFriendly | 1–2 | Friendly |
| 2016-03-26 | AnguillavPuerto RicoCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 2016-03-13 | Sint MaartenvAnguillaFriendly | 2–0 | Friendly |
| 2015-03-29 | AnguillavNicaraguaFIFA World Cup qualification | 0–3 | FIFA World Cup qualification |
| 2015-03-23 | NicaraguavAnguillaFIFA World Cup qualification | 5–0 | FIFA World Cup qualification |
| 2014-09-05 | Saint Vincent and the GrenadinesvAnguillaCFU Caribbean Cup qualification | 4–0 | CFU Caribbean Cup qualification |
| 2012-10-14 | Trinidad and TobagovAnguillaCFU Caribbean Cup qualification | 10–0 | CFU Caribbean Cup qualification |
| 2012-10-12 | French GuianavAnguillaCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 2012-07-07 | British Virgin IslandsvAnguillaFriendly | 1–0 | Friendly |
| 2011-07-10 | Dominican RepublicvAnguillaFIFA World Cup qualification | 4–0 | FIFA World Cup qualification |
| 2011-07-08 | Dominican RepublicvAnguillaFIFA World Cup qualification | 2–0 | FIFA World Cup qualification |