Caribbean Championship 2017, Qualifying tournament, First Round, Group 5 |
 | 26.03.2016 |  | Anguilla | – | Puerto Rico |  | 0:4 (0:2) |
| The Valley Raymond E. Guishard Technical Centre |
Caribbean Championship 2017, Qualifying tournament, First Round, Group 5 |
| 22.03.2016 |  | Guyana | – | Anguilla | | 7:0 (5:0) |
| Georgetown |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 5 |
| 07.09.2014 | | Anguilla | – | Dominican Republic |  | 0:10 (0:4) |
| St. John's |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 5 |
| 05.09.2014 |  | Saint Vincent and Grenadines | – | Anguilla | | 4:0 (2:0) |
| St. John's |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 5 |
| 03.09.2014 |  | Antigua and Barbuda | – | Anguilla | | 6:0 (3:0) |
| St. John's |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 5 |
| 14.10.2012 | | Anguilla | – | Trinidad and Tobago |  | 0:10 (0:7) |
| Bassterre |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 5 |
| 12.10.2012 | | Anguilla | – | French Guiana |  | 1:4 (0:3) |
| Bassterre |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 5 |
| 10.10.2012 |  | Saint Kitts and Nevis | – | Anguilla | | 2:0 (2:0) |
| Bassterre |
Caribbean Championship 2010, Qualifying tournament, First Round, Group A |
| 04.10.2010 |  | Cayman Islands | – | Anguilla | | 4:1 (1:1) |
| Bayamón |
Caribbean Championship 2010, Qualifying tournament, First Round, Group A |
| 02.10.2010 | | Puerto Rico | – | Anguilla | | 3:1 (2:0) |
| Bayamón |
Caribbean Championship 2008, Qualifying tournament, First Round, Group E |
| 19.09.2008 |  | Martinique | – | Anguilla | | 3:1 (2:0) |
| Fort-de-France |
Caribbean Championship 2008, Qualifying tournament, First Round, Group E |
| 17.09.2008 | | Saint Vincent and Grenadines | – | Anguilla | | 3:1 (2:1) |
| Fort-de-France |
Caribbean Cup 2007, Qualifying tournament, First Round, Group B |
| 24.09.2006 |  | Barbados | – | Anguilla | | 7:1 (3:0) |
| St. John's |
Caribbean Cup 2007, Qualifying tournament, First Round, Group B |
| 22.09.2006 | | Anguilla | – | Saint Kitts and Nevis | | 1:6 (1:2) |
| St. John's |
Caribbean Cup 2007, Qualifying tournament, First Round, Group B |
| 20.09.2006 | | Antigua and Barbuda | – | Anguilla | | 5:3 (3:1) |
| St. John's |
Caribbean Cup 2001, Qualifying tournament, Preliminary round, group 1 |
| 10.02.2001 |  | Sint Maarten | – | Anguilla | | 3:1 (2:0) |
| Marigot |
Caribbean Cup 1998, Qualifying tournament, Group 4 |
| 19.04.1998 | | Anguilla | – | Guyana | | 0:14 |
| St. John's |
Caribbean Cup 1998, Qualifying tournament, Group 4 |
| 17.04.1998 | | Antigua and Barbuda | – | Anguilla | | 7:0 |
| St. John's |
Caribbean Cup 1998, Qualifying tournament, Group 4 |
| 15.04.1998 | | Anguilla | – | Grenada |  | 1:14 |
| St. John's |
Caribbean Cup 1997, Qualifying tournament, Group 4 |
| 06.04.1997 |  | Dominica | – | Anguilla | | 5:0 |
| Roseau |
Caribbean Cup 1997, Qualifying tournament, Group 4 |
| 04.04.1997 |  | British Virgin Islands | – | Anguilla | | 4:1 |
| Roseau |
Caribbean Cup 1997, Qualifying tournament, Group 4 |
| 02.04.1997 | | Sint Maarten | – | Anguilla | | 3:0 |
| Roseau |
Caribbean Cup 1996, Qualifying tournament, Group 2 |
| 29.03.1996 | | Sint Maarten | – | Anguilla | | 4:0 |
| Bassterre |
Caribbean Cup 1996, Qualifying tournament, Group 2 |
| 27.03.1996 | | Saint Kitts and Nevis | – | Anguilla | | 8:0 |
| Bassterre |
Caribbean Cup 1995, Qualifying tournament, Group 4, Round 1 |
| 02.04.1995 | | Anguilla | – | Montserrat |  | 0:1 |
| The Valley |
Caribbean Cup 1995, Qualifying tournament, Group 4, Round 1 |
| 26.03.1995 | | Montserrat | – | Anguilla | | 3:2 |
| Woodlands |
Caribbean Cup 1994, Qualifying tournament, Group 2 |
| 06.03.1994 | | Saint Vincent and Grenadines | – | Anguilla | | 2:0 |
| Kingstown |
Caribbean Cup 1994, Qualifying tournament, Group 2 |
| 04.03.1994 |  | Guadeloupe | – | Anguilla | | 9:0 |
| Kingstown |
Caribbean Cup 1993, Qualifying tournament, Group 4 |
| 06.04.1993 | | Anguilla | – | Sint Maarten | | 0:1 |
| The Valley |
Caribbean Cup 1993, Qualifying tournament, Group 4 |
| 04.04.1993 | | Anguilla | – | Antigua and Barbuda | | 0:4 |
| The Valley |
Caribbean Cup 1992, Qualifying tournament, Group 6 |
| 09.05.1992 |  | Cuba | – | Anguilla | | 5:0 |
| |
Caribbean Cup 1992, Qualifying tournament, Group 6 |
| 02.05.1992 | | Anguilla | – | Cuba | | 0:3 |
| |
Caribbean Cup 1991, Qualifying tournament, Group 6 |
| 09.03.1991 |  | Saint Lucia | – | Anguilla | | 6:0 |
| Castries |
Caribbean Cup 2005, Qualifying tournament, Group F, Preliminary Round |
| | | Antigua and Barbuda | – | Anguilla | | +:- |
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