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| 5.7.08 | U-20 Qualifying |
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| Grp E | Netherlands Antilles vs St. Martin | 20:30 |
| Grp E | Antigua & Barbuda vs Anguilla | 18:30 |
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| Friendlies |
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| Women | Sweden vs USA | |
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| 6.7.08 | Champions League Qualifying |
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| Men | CSD Municipal vs Deportivo Jalapa | |
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| 8.7.08 | Champions League Qualifying |
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| Men | CD Olimpia vs CD Marathon | 19:00 |
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| 9.7.08 | Champions League Qualifying |
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| Men | Vancouver Whitecaps vs Toronto FC | TBD |
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| 10.7.08 | Friendlies |
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| Women | Canada vs Brazil | |
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| 13.7.08 | Friendlies |
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| Women | USA vs Brazil | |
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| 16.7.08 | U-20 Qualifying |
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| Grp C | Aruba vs St. Kitts | 20:30 |
| Grp C | Suriname vs Dominica | 18:30 |
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| Friendlies |
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| Women | USA vs Brazil | |
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| 17.7.08 | Beach Soccer |
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| Grp B | Portugal vs El Salvador | 17:45 |
|
| U-17 Women |
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| Grp B | Mexico vs Jamaica | 19:00 |
| Grp B | Puerto Rico vs Canada | 17:00 |
| Grp A | Trinidad & Tobago vs El Salvador | 19:00 |
| Grp A | Costa Rica vs USA | 17:00 |
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| 18.7.08 | U-20 Qualifying |
|
| Grp C | Aruba vs Dominica | 20:30 |
| Grp C | St. Kitts vs Suriname | 18:30 |
|
| Beach Soccer |
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| Grp D | Mexico vs Japan | 16:15 |
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| 19.7.08 | Beach Soccer |
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| Grp B | El Salvador vs Italy | 16:15 |
|
| U-17 Women |
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| Grp B | Canada vs Jamaica | 18:00 |
| Grp B | Mexico vs Puerto Rico | 16:00 |
| Grp A | USA vs El Salvador | 16:00 |
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| 20.7.08 | U-20 Qualifying |
|
| Grp C | Aruba vs Suriname | 20:30 |
| Grp C | Dominica vs St. Kitts | 18:30 |
|
| Beach Soccer |
|
| Grp D | Spain vs Mexico | 14:45 |
|
| U-17 Women |
|
| Grp A | Trinidad & Tobago vs Costa Rica | 18:00 |
|
| 21.7.08 | Beach Soccer |
|
| Grp B | El Salvador vs Solomon Islands | 16:15 |
|
| U-17 Women |
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| Grp B | Canada vs Mexico | 19:00 |
| Grp B | Jamaica vs Puerto Rico | 17:00 |
|
| 22.7.08 | Beach Soccer |
|
| Grp D | Brazil vs Mexico | 19:15 |
|
| U-17 Women |
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| Grp A | Trinidad & Tobago vs USA | 19:00 |
| Grp A | El Salvador vs Costa Rica | 17:00 |
|
| Champions League Qualifying |
|
| Men | Toronto FC vs Impact de Montreal | TBD |
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| 23.7.08 | U-20 Qualifying |
|
| Grp B | Cayman Islands vs Bermuda | 19:00 |
| Grp B | Jamaica vs Puerto Rico | 17:00 |
|
| 24.7.08 | U-17 Women |
|
| SF | A1 vs B2 | 19:00 |
| SF | B1 vs A2 | 17:00 |
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| 25.7.08 | U-20 Qualifying |
|
| Grp B | Cayman Islands vs Puerto Rico | 19:00 |
| Grp B | Bermuda vs Jamaica | 17:00 |
|
| 26.7.08 | U-17 Women |
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| Final | vs | 18:00 |
| 3rd | vs | 16:00 |
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| 27.7.08 | U-20 Qualifying |
|
| Grp B | Puerto Rico vs Bermuda | 17:00 |
| Grp B | Cayman Islands vs Jamaica | 19:00 |
|
| CFU Championship |
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| Grp A | Netherlands Antilles vs Grenada | 20:00 |
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| 29.7.08 | CFU Championship |
|
| Grp A | Grenada vs St. Lucia | 20:00 |
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| 31.7.08 | CFU Championship |
|
| Grp A | Netherlands Antilles vs St. Lucia | 20:00 |
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| 6.8.08 | CFU Championship |
|
| Grp B | Suriname vs Guyana | |
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| 8.8.08 | CFU Championship |
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| Grp B | Aruba vs Suriname | |
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| 10.8.08 | CFU Championship |
|
| Grp B | Guyana vs Aruba | |
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| 20.8.08 | World Cup |
|
| Grp C | Haiti vs Suriname | |
| Grp C | Costa Rica vs El Salvador | |
| Grp B | Mexico vs Honduras | |
| Grp B | Canada vs Jamaica | |
| Grp A | Guatemala vs USA | |
| Grp A | Cuba vs Trinidad & Tobago | |
|
| 27.8.08 | CFU Championship |
|
| Grp C | Cayman Islands vs St. Martin | 19:15 |
| Grp C | Bermuda vs Antigua & Barbuda | 17:00 |
|
| 29.8.08 | CFU Championship |
|
| Grp C | Cayman Islands vs Bermuda | 19:15 |
| Grp C | Cayman Islands vs Bermuda | 19:15 |
| Grp C | Antigua & Barbuda vs St. Martin | 17:00 |
|
| 31.8.08 | CFU Championship |
|
| Grp C | Cayman Islands vs Antigua & Barbuda | 19:15 |
| Grp C | St. Martin vs Bermuda | 17:00 |
|
| 6.9.08 | World Cup |
|
| Grp C | Costa Rica vs Suriname | |
| Grp C | El Salvador vs Haiti | |
| Grp B | Canada vs Honduras | |
| Grp B | Jamaica vs Mexico | |
| Grp A | Cuba vs USA | |
| Grp A | Trinidad & Tobago vs Guatemala | |
| Grp A | Trinidad & Tobago vs Guatemala | |
|
| 10.9.08 | World Cup |
|
| Grp C | Haiti vs Costa Rica | |
| Grp C | Suriname vs El Salvador | |
| Grp B | Mexico vs Canada | |
| Grp B | Honduras vs Jamaica | |
| Grp A | Guatemala vs Cuba | |
| Grp A | USA vs Trinidad & Tobago | |
|
| 15.9.08 | CFU Championship |
|
| Grp E | Martinique vs St. Vincent & The Grenadines | 20:00 |
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| 17.9.08 | CFU Championship |
|
| Grp E | St. Vincent & The Grenadines vs Anguilla | 20:00 |
|
| 19.9.08 | CFU Championship |
|
| Grp E | Martinique vs Anguilla | 20:00 |
|
| 11.10.08 | World Cup |
|
| Grp C | Suriname vs Costa Rica | |
| Grp C | Haiti vs El Salvador | |
| Grp B | Honduras vs Canada | |
| Grp B | Mexico vs Jamaica | |
| Grp A | USA vs Cuba | |
| Grp A | Guatemala vs Trinidad & Tobago | |
|
| 15.10.08 | World Cup |
|
| Grp C | Costa Rica vs Haiti | |
| Grp C | El Salvador vs Suriname | |
| Grp B | Canada vs Mexico | |
| Grp B | Jamaica vs Honduras | |
| Grp A | Cuba vs Guatemala | |
| Grp A | Trinidad & Tobago vs USA | |
|
| 19.11.08 | World Cup |
|
| Grp C | Suriname vs Haiti | |
| Grp C | El Salvador vs Costa Rica | |
| Grp B | Honduras vs Mexico | |
| Grp B | Jamaica vs Canada | |
| Grp A | USA vs Guatemala | |
| Grp A | Trinidad & Tobago vs Cuba | |
|