Caribbean Championship 2017, Qualifying tournament, Second round, group 4 |
 | 19.06.2016 |  | French Guiana | – | Bermuda |  | 3:0 (0:0) |
| Remire-Montjoly |
Caribbean Championship 2017, Qualifying tournament, Second round, group 4 |
| 04.06.2016 | | Bermuda | – | Dominican Republic |  | 0:1 (0:1) |
| Hamilton |
Caribbean Championship 2017, Qualifying tournament, First Round, Group 3 |
| 26.03.2016 | | Bermuda | – | French Guiana | | 2:1 (1:1) |
| Hamilton |
Caribbean Championship 2017, Qualifying tournament, First Round, Group 3 |
| 22.03.2016 |  | Cuba | – | Bermuda | | 2:1 (1:0) |
| La Habana |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 1 |
| 11.09.2012 |  | St. Martin | – | Bermuda | | 0:8 (0:2) |
| Port-au-Prince |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 1 |
| 09.09.2012 |  | Haiti | – | Bermuda | | 3:1 (3:0) |
| Port-au-Prince |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 1 |
| 07.09.2012 | | Bermuda | – | Puerto Rico |  | 1:2 (0:0) |
| Port-au-Prince |
Caribbean Championship 2008, Qualifying tournament, First Round, Group C |
| 31.08.2008 |  | Cayman Islands | – | Bermuda | | 0:0 |
| George Town |
Caribbean Championship 2008, Qualifying tournament, First Round, Group C |
| 30.08.2008 |  | Sint Maarten | – | Bermuda | | 0:7 (0:3) |
| George Town |
Caribbean Championship 2008, Qualifying tournament, First Round, Group C |
| 27.08.2008 | | Bermuda | – | Antigua and Barbuda |  | 0:4 (0:2) |
| George Town |
Caribbean Cup 2007, Qualifying tournament, Second round, playoff |
| 09.01.2007 | | Bermuda | – | Haiti | | 0:3 (0:1) |
| Couva |
Caribbean Cup 2007, Qualifying tournament, Second round, playoff |
| 07.01.2007 | | Haiti | – | Bermuda | | 2:0 (1:0) |
| Couva |
Caribbean Cup 2007, Qualifying tournament, Second round, group G |
| 23.11.2006 |  | Barbados | – | Bermuda | | 1:1 (1:1) |
| Bridgetown |
Caribbean Cup 2007, Qualifying tournament, Second round, group G |
| 21.11.2006 |  | Bahamas | – | Bermuda | | 0:4 (0:3) |
| Bridgetown |
Caribbean Cup 2007, Qualifying tournament, Second round, group G |
| 19.11.2006 | | Bermuda | – | Saint Vincent and Grenadines |  | 0:3 (0:0) |
| Bridgetown |
Caribbean Cup 2007, Qualifying tournament, First Round, Group C |
| 01.10.2006 | | Bermuda | – | British Virgin Islands |  | 3:0 |
| Charlotte Amalie |
Caribbean Cup 2007, Qualifying tournament, First Round, Group C |
| 29.09.2006 | | Bermuda | – | Dominican Republic | | 3:1 (1:0) |
| Charlotte Amalie |
Caribbean Cup 2007, Qualifying tournament, First Round, Group C |
| 27.09.2006 |  | US Virgin Islands | – | Bermuda | | 0:6 (0:4) |
| Charlotte Amalie |
Caribbean Cup 2005, Qualifying tournament, Group E |
| 28.11.2004 | | British Virgin Islands | – | Bermuda | | 2:0 (2:0) |
| Kingstown |
Caribbean Cup 2005, Qualifying tournament, Group E |
| 26.11.2004 | | Saint Vincent and Grenadines | – | Bermuda | | 3:3 (1:1) |
| Kingstown |
Caribbean Cup 2005, Qualifying tournament, Group E |
| 24.11.2004 | | Bermuda | – | Cayman Islands | | 2:1 (2:0) |
| Kingstown |
Caribbean Cup 1999, Qualifying tournament, Group 1 |
| 09.05.1999 | | Bermuda | – | Cuba | | 1:2 |
| Hamilton |
Caribbean Cup 1999, Qualifying tournament, Group 1 |
| 07.05.1999 | | Bermuda | – | Cayman Islands | | 4:1 |
| Hamilton |
Caribbean Cup 1999, Qualifying tournament, Group 1 |
| 05.05.1999 | | Bermuda | – | Bahamas | | 6:0 (4:0) |
| Hamilton |
Caribbean Cup 1998, Qualifying tournament, Group 6 |
| 10.05.1998 | | Cayman Islands | – | Bermuda | | 2:0 |
| |
Caribbean Cup 1998, Qualifying tournament, Group 6 |
| 08.05.1998 | | Bermuda | – | Cuba | | 1:2 |
| |
Caribbean Cup 1997, Qualifying tournament, Group 2 |
| 23.03.1997 |  | Jamaica | – | Bermuda | | 3:2 |
| Kingston |
Caribbean Cup 1997, Qualifying tournament, Group 2 |
| 21.02.1997 | | Jamaica | – | Bermuda | | 1:0 |
| Kingston |
Caribbean Cup 2005, Qualifying tournament, Group E, Preliminary Round |
| | | Bermuda | – | Aruba |  | +:- |
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