| Date | League | Home | Results | Away | HT | HDP | W/L |
|---|---|---|---|---|---|---|---|
| 2023-11-21 05:00 | CONCACAF NL | Montserrat | 0:0 | Barbados | 0:0 | 1.25 | Lose |
| 2023-09-09 07:00 | CONCACAF NL | Barbados | 2:3 | Montserrat | 2:1 | 0.25 | Win |
| 2010-10-09 | CONCACAF NL | Barbados | 5:0 | Montserrat | 2:0 |
| Date | League | Home | Results | Away | HT | HDP | W/L |
|---|---|---|---|---|---|---|---|
| 2024-10-14 03:00 | CONCACAF NL | Montserrat | 0:1 | Bonaire | 0:1 | 1 | Win |
| 2024-10-11 04:00 | CONCACAF NL | Bonaire | 0:1 | Montserrat | 0:0 | -0.25 | Win |
| 2024-09-09 04:00 | CONCACAF NL | St. Vincent Grenadines | 2:0 | Montserrat | 1:0 | -0.25 | Lose |
| 2024-09-06 04:00 | CONCACAF NL | Montserrat | 1:4 | El Salvador | 1:1 | -1.5 | Win |
| 2023-11-18 10:00 | CONCACAF NL | Dominican Republic | 0:0 | Montserrat | 0:0 | ||
| 2023-10-17 10:00 | CONCACAF NL | Nicaragua | 3:0 | Montserrat | 2:0 | 2.25 | Lose |
| 2023-10-14 03:00 | CONCACAF NL | Montserrat | 0:3 | Nicaragua | 0:1 | -1 | Win |
| 2023-09-12 07:00 | CONCACAF NL | Montserrat | 0:3 | Dominican Republic | 0:2 | -0.75 | Win |
| 2022-06-12 07:30 | CONCACAF NL | Montserrat | 3:2 | Bermuda | 0:0 | -0.5 | Lose |
| 2022-06-15 06:00 | CONCACAF NL | Bermuda | 0:0 | Montserrat | 0:0 | 0.75 | Win |
| 2023-03-29 07:00 | CONCACAF NL | Guyana | 0:0 | Montserrat | 0:0 | 0.5 | Win |
| 2022-06-05 07:30 | CONCACAF NL | Montserrat | 1:2 | Guyana | 1:0 | -0.5 | Win |
| 2022-06-08 05:00 | CONCACAF NL | Haiti | 3:2 | Montserrat | 3:1 | 1.5 | Win |
| 2023-03-26 05:00 | CONCACAF NL | Montserrat | 0:0 | Haiti | 0:0 | -1 | Lose |
| 2021-07-03 10:15 | CONCACAF NL | Trinidad and Tobago | 6:1 | Montserrat | 3:0 | 1.25 | Lose |
| 2021-06-09 07:05 | CONCACAF NL | Grenada | 1:2 | Montserrat | 0:0 | -0.5 | Win |
| 2021-06-03 05:00 | CONCACAF NL | Montserrat | 4:0 | US Virgin Islands | 1:0 | 4.5 | Win |
| 2021-03-29 06:00 | CONCACAF NL | Montserrat | 1:1 | El Salvador | 0:1 | -1.5 | Lose |
| 2021-03-25 06:00 | CONCACAF NL | Antigua Barbuda | 2:2 | Montserrat | 2:2 | 1.5 | Win |
| 2019-09-11 | CONCACAF NL | Montserrat | 1:1 | St. Lucia | 1:0 | 0.5 | Win |
| 2019-11-20 | CONCACAF NL | Montserrat | 1:0 | St. Lucia | 1:0 | 0 | Lose |
| 2019-11-17 | CONCACAF NL | El Salvador | 1:0 | Montserrat | 0:0 | 2.5 | Win |
| 2019-10-16 | CONCACAF NL | Dominican Republic | 0:0 | Montserrat | 0:0 | 1 | Win |
| 2019-10-13 | CONCACAF NL | Montserrat | 0:2 | El Salvador | 0:1 | ||
| 2019-09-08 | CONCACAF NL | Montserrat | 2:1 | Dominican Republic | 1:1 | -0.5 | Lose |
| 2019-03-23 | CONCACAF NL | Cayman Islands | 1:2 | Montserrat | 0:1 | ||
| 2018-11-17 | CONCACAF NL | Aruba | 0:2 | Montserrat | 0:1 | 0 | Win |
| 2018-10-15 | CONCACAF NL | Montserrat | 1:0 | Belize | 0:0 | ||
| 2018-09-09 | CONCACAF NL | Montserrat | 1:2 | El Salvador | 1:0 | ||
| 2015-03-28 | CONCACAF NL | Curacao | 2:1 | Montserrat | 2:1 |
| Date | League | Home | Results | Away | HT | HDP | W/L |
|---|---|---|---|---|---|---|---|
| 2024-10-16 08:00 | CONCACAF NL | Barbados | 6:2 | Bahamas | 3:2 | 1.25 | Lose |
| 2024-10-10 08:00 | CONCACAF NL | US Virgin Islands | 0:5 | Barbados | 0:2 | -1.75 | Win |
| 2024-09-11 04:00 | CONCACAF NL | Barbados | 3:0 | US Virgin Islands | 1:0 | 1.5 | Lose |
| 2024-09-08 04:00 | CONCACAF NL | Bahamas | 2:3 | Barbados | 1:1 | -0.25 | Win |
| 2023-11-18 10:00 | CONCACAF NL | Barbados | 0:0 | Nicaragua | 0:0 | ||
| 2023-10-17 10:00 | CONCACAF NL | Dominican Republic | 5:2 | Barbados | 2:1 | 2.25 | Lose |
| 2023-10-14 08:00 | CONCACAF NL | Barbados | 0:5 | Dominican Republic | 0:3 | -0.5 | Win |
| 2023-09-12 10:00 | CONCACAF NL | Nicaragua | 5:1 | Barbados | 3:0 | 2.75 | Lose |
| 2023-06-19 05:00 | CONCACAF NL | Honduras | 0:0 | Barbados | 0:0 | ||
| 2023-03-09 08:00 | CONCACAF NL | Barbados | 0:0 | St. Vincent Grenadines | 0:0 | ||
| 2023-02-27 07:10 | CONCACAF NL | Grenada | 2:2 | Barbados | 1:1 | ||
| 2023-02-25 07:00 | CONCACAF NL | Grenada | 2:2 | Barbados | 1:1 | ||
| 2023-02-23 07:00 | CONCACAF NL | Grenada | 1:1 | Barbados | 0:0 | ||
| 2022-06-10 06:00 | CONCACAF NL | Barbados | 0:1 | Guadeloupe | 0:1 | -1.75 | Lose |
| 2022-06-13 06:00 | CONCACAF NL | Guadeloupe | 2:1 | Barbados | 2:0 | 2 | Win |
| 2023-03-27 04:00 | CONCACAF NL | Antigua Barbuda | 1:2 | Barbados | 1:0 | 1 | Win |
| 2022-06-03 07:30 | CONCACAF NL | Barbados | 0:1 | Antigua Barbuda | 0:0 | -0.25 | Win |
| 2023-03-24 07:00 | CONCACAF NL | Barbados | 0:1 | Cuba | 0:1 | -1.5 | Lose |
| 2022-06-06 04:00 | CONCACAF NL | Cuba | 3:0 | Barbados | 2:0 | 1.75 | Lose |
| 2022-03-26 07:00 | CONCACAF NL | Trinidad and Tobago | 9:0 | Barbados | 4:0 | ||
| 2022-01-31 05:30 | CONCACAF NL | Guyana | 0:0 | Barbados | 0:0 | ||
| 2022-01-29 06:25 | CONCACAF NL | Suriname | 1:0 | Barbados | 0:0 | ||
| 2021-07-03 08:00 | CONCACAF NL | Bermuda | 8:1 | Barbados | 4:1 | 0.25 | Lose |
| 2021-06-09 09:00 | CONCACAF NL | Barbados | 1:1 | Dominica | 0:0 | ||
| 2021-06-05 07:00 | CONCACAF NL | Dominican Republic | 1:1 | Barbados | 0:1 | 1.25 | Win |
| 2021-03-31 07:35 | CONCACAF NL | Barbados | 1:0 | Anguilla | 0:0 | 2.75 | Win |
| 2021-03-26 08:00 | CONCACAF NL | Panama | 1:0 | Barbados | 0:0 | 1.5 | Win |
| 2020-01-11 | CONCACAF NL | Barbados | 1:4 | Canada | 0:2 | -2.5 | Win |
| 2020-01-08 | CONCACAF NL | Barbados | 1:4 | Canada | 1:3 | -2 | Win |
| 2019-11-20 | CONCACAF NL | Barbados | 3:0 | Cayman Islands | 1:0 |
