| #1 | 05.03.2000 | Anguilla | - | Bahamas | 1:3 | ||||
| #2 | 19.03.2000 | Bahamas | - | Anguilla | 2:1 | ||||
| #3 | 19.03.2004 | Dom. Republiek | - | Anguilla | 0:0 | ||||
| #4 | 21.03.2004 | Anguilla | - | Dom. Republiek | 0:6 |  |
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| #5 | 22.09.2006 | Anguilla | - | St. Kitts & Nevis | 1:6 | ||||
| #6 | 24.09.2006 | Barbados | - | Anguilla | 7:1 |  |
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| #7 | 07.02.2008 | El Salvador | - | Anguilla | 12:0 | ||||
| #8 | 27.03.2008 | Anguilla | - | El Salvador | 0:4 | |
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| #9 | 03.10.2010 | Puerto Rico | - | Anguilla | 3:1 | ||||
| #10 | 05.10.2010 | Cayman Eilanden | - | Anguilla | 4:1 | ||||
| #11 | 07.10.2010 | Anguilla | - | St. Maarten | 2:1 | ||||
| #12 | 18.06.2011 | Anguilla | - | Maagdeneilanden | 0:0 | ||||
| #13 | 08.07.2011 | Anguilla | - | Dom. Republiek | 0:2 | ||||
| #14 | 10.07.2011 | Dom. Republiek | - | Anguilla | 4:0 | ||||
| #15 | 24.03.2015 | Nicaragua | - | Anguilla | 5:0 | ||||
| #16 | 29.03.2015 | Anguilla | - | Nicaragua | 0:3 | ||||
| #17 | 07.09.2018 | Anguilla | - | Frans Guyana | 0:5 | ||||
| #18 | 15.10.2018 | Nicaragua | - | Anguilla | 6:0 | |
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| #19 | 19.11.2018 | Bahamas | - | Anguilla | 1:1 |
Anguilla