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| Location | Event | Date/Time | Teams | Pool | Game | Man Schd |
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| Fairfield Hills | 14 & Under Jimmy Fund | 6/22/2009 05:00 PM | Newtown Gold, Ridgefield 13 A | | 10 | Yes |
| Fairfield Hills | District 4: 13 Prep District Tournament | 7/5/2009 12:00 PM | Bethel, New Milford | | 3 | Yes |
| Fairfield Hills | District 4: 13 Prep District Tournament | 7/6/2009 05:00 PM | Newtown Blue | | 5 | Yes |
| Fairfield Hills | District 4: 13 Prep District Tournament | 7/7/2009 05:00 PM | | | 8 | Yes |
| Fairfield Hills | District 4: 13 Prep District Tournament | 7/8/2009 05:00 PM | | | 9 | Yes |
| Fairfield Hills | District 4: 13 Prep District Tournament | 7/10/2009 05:00 PM | | | 13 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/20/2009 10:00 AM | Danbury 13 B, Ridgefield 13 A | | 3 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/20/2009 01:00 PM | Danbury 14, Bethel 14 | | 1 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/20/2009 04:00 PM | Ridgefield 13 B, Newtown Blue | | 5 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/22/2009 05:00 PM | Danbury 14, Newtown 14 | | 6 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/24/2009 05:00 PM | Danbury 13 B, Bethel 14 | | 12 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/25/2009 05:00 PM | Brookfield, Newtown Blue | | 9 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/25/2009 05:00 PM | Danbury 14, Fairfield 14 | | 15 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/27/2009 10:00 AM | Danbury 13 A, Newtown Blue | | 16 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/28/2009 11:00 AM | Danbury 14, Newtown Blue | | 21 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/29/2009 05:00 PM | | | 23 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 6/30/2009 05:00 PM | | | 24 | Yes |
| Newtown High School | 14 & Under Jimmy Fund | 7/1/2009 05:00 PM | | | 25 | Yes |
| Newtown High School | District 4: 13 Prep District Tournament | 7/5/2009 12:00 PM | Brookfield, Newtown Gold | | 1 | Yes |
| Newtown High School | District 4: 13 Prep District Tournament | 7/9/2009 05:00 PM | | | 12 | Yes |
| Newtown High School | District 4: 13 Prep District Tournament | 7/13/2009 05:00 PM | | | 18 | Yes |
| Newtown Middle School | 14 & Under Jimmy Fund | 6/20/2009 10:00 AM | Danbury 13 A, Newtown Gold | | 4 | Yes |
| Newtown Middle School | 14 & Under Jimmy Fund | 6/20/2009 01:00 PM | Fairfield 14, New Milford 14 | | 2 | Yes |
| Newtown Middle School | 14 & Under Jimmy Fund | 6/22/2009 05:00 PM | Ridgefield 14, Fairfield 14 | | 7 | Yes |
| Newtown Middle School | 14 & Under Jimmy Fund | 6/23/2009 05:00 PM | Ridgefield 14, Ridgefield 13 B | | 11 | Yes |
| Newtown Middle School | 14 & Under Jimmy Fund | 6/27/2009 10:00 AM | Brookfield, New Milford 14 | | 13 | Yes |
| Newtown Middle School | 14 & Under Jimmy Fund | 6/27/2009 01:00 PM | New Milford 14, Bethel 14 | | 18 | Yes |
| Newtown Middle School | 14 & Under Jimmy Fund | 6/27/2009 04:00 PM | Fairfield 14, Bethel 14 | | 20 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 6/11/2009 05:00 PM | | | 11 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 6/20/2009 01:00 PM | | | 16 | Yes |
| Walnut Tree | 14 & Under Jimmy Fund | 6/22/2009 05:00 PM | Danbury 13 A, Danbury 13 B | | 8 | Yes |
| Walnut Tree | 14 & Under Jimmy Fund | 6/27/2009 10:00 AM | Newtown 14, Ridgefield 13 A | | 14 | Yes |
| Walnut Tree | 14 & Under Jimmy Fund | 6/27/2009 11:00 AM | Ridgefield 14, Newtown 14 | | 17 | Yes |
| Walnut Tree | 14 & Under Jimmy Fund | 6/28/2009 11:00 AM | Ridgefield 14, Danbury 13 A | | 19 | Yes |
| Walnut Tree | 14 & Under Jimmy Fund | 6/28/2009 02:00 PM | Bethel 14 | | 22 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 7/5/2009 12:00 PM | Danbury 13 A, Aspetuck | | 2 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 7/5/2009 03:00 PM | Southbury, New Fairfield | | 4 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 7/6/2009 05:00 PM | Ridgefield 13 A | | 6 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 7/7/2009 05:00 PM | | | 7 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 7/8/2009 05:00 PM | | | 10 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 7/10/2009 05:00 PM | | | 14 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 7/11/2009 10:00 AM | | | 15 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 7/12/2009 12:00 PM | | | 17 | Yes |
| Walnut Tree | District 4: 13 Prep District Tournament | 7/14/2009 05:00 PM | | | 19 | Yes |