| #1 | 28.03.2015 | Curaçao | - | Montserrat | 2:1 |  |
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| #2 | 01.04.2015 | Montserrat | - | Curaçao | 2:2 | ||||
| #3 | 15.10.2018 | Montserrat | - | Belize | 1:0 |  |
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| #4 | 17.11.2018 | Aruba | - | Montserrat | 0:2 | ||||
| #5 | 23.03.2019 | Kaimaninseln | - | Montserrat | 1:2 | ||||
| #6 | 07.09.2019 | Montserrat | - | Dom. Republik | 2:1 | ||||
| #7 | 24.03.2021 | Antigua & Barbuda | - | Montserrat | 2:2 | |
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| #8 | 29.03.2021 | Montserrat | - | El Salvador | 1:1 | |
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| #9 | 02.06.2021 | Montserrat | - | US Jungferninseln | 4:0 | ||||
| #10 | 09.06.2021 | Grenada | - | Montserrat | 1:2 | |
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| #11 | 03.07.2021 | Trinidad & Tobago | - | Montserrat | 6:1 | |
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| #12 | 07.06.2022 | Haiti | - | Montserrat | 3:2 | |
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| #13 | 12.06.2022 | Montserrat | - | Bermuda | 3:2 | |
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| #14 | 09.09.2023 | Barbados | - | Montserrat | 2:3 | |
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| #15 | 12.09.2023 | Dom. Republik | - | Montserrat | 3:0 | ||||
| #16 | 13.10.2023 | Montserrat | - | Nicaragua | 0:3 |  |
England