| (0 to 0) Cayman Islands 1(1) - 3.5(2) Montserrat (0 to 0): 22MAR2019 |
| (0 to 0) Aruba KN 0(0) - 3.5(2) Montserrat (0 to 0): 16NOV2018 |
| (0 to 0) Montserrat 2(1) - 0(0) Belize (0 to 0): 14OCT2018 |
| (0 to 0) Montserrat 6.5(1) - 2(2) Salvador (0 to 0): 08SEP2018 |
| (0 to 0) Montserrat 3.5(2) - 2(2) Curacao KN (0 to 0): 31MAR2015 |
| (0 to 0) Curacao KN 2(2) - 2.5(1) Montserrat (0 to 0): 27MAR2015 |
| (0 to 0) Montserrat 1(0) - 0(0) Bonaire NDL KN (0 to 0): 03JUN2014 |
| (0 to 0) Montserrat 2.5(1) - 0(0) American Virgin Islands (0 to 0): 30MAY2014 |
| (0 to 0) Montserrat 8(7) - 0(0) British Virgin Islands (0 to 0): 09SEP2012 |
| (0 to 0) Martinique FRA 5(5) - 2.5(0) Montserrat (0 to 0): 07SEP2012 |
| (0 to 0) Suriname 7(7) - 3(1) Montserrat (0 to 0): 05SEP2012 |
| (0 to 0) Belize 3(3) - 2(1) Montserrat (0 to 0): 17JUL2011 |
| (0 to 0) Montserrat 3(2) - 5(5) Belize (0 to 0): 15JUN2011 |
| (0 to 0) Saint Kitts Nevis 4(4) - 1(0) Montserrat (0 to 0): 10OCT2010 |
| (0 to 0) Barbados 5(5) - 2(0) Montserrat (0 to 0): 08OCT2010 |
| (0 to 0) Saint Vincent Grenadines 7(7) - 1(0) Montserrat (0 to 0): 06OCT2010 |
| (0 to 0) Montserrat 2(1) - 7(7) Suriname (0 to 0): 26MAR2008 |
| (0 to 0) Saint Lucia 3(3) - 1(0) Montserrat (0 to 0): 04NOV2004 |
| (0 to 0) Antigua Barbuda 5(5) - 5(4) Montserrat (0 to 0): 02NOV2004 |
| (0 to 0) Saint Kitts Nevis 6(6) - 2(1) Montserrat (0 to 0): 31OCT2004 |
| (0 to 0) Montserrat 2(0) - 7(7) Bermuda (0 to 0): 21MAR2004 |
| (0 to 0) Bermuda 13(13) - 2(0) Montserrat (0 to 0): 28FEB2004 |
| (0 to 0) Anguilla 4(4) - 1.5(1) Montserrat (0 to 0): 08FEB2001 |
| (0 to 0) Montserrat 6.5(1) - 3(3) Dominicana (0 to 0): 19MAR2000 |
| (0 to 0) Dominicana 3(3) - 5.5(0) Montserrat (0 to 0): 05MAR2000 |
| (0 to 0) Montserrat 0.5(0) - 11(11) Saint Vincent Grenadines (0 to 0): 07MAY1995 |
| (0 to 0) Saint Vincent Grenadines 9(9) - 0.5(0) Montserrat (0 to 0): 30APR1995 |