| 270016 | 4/2/2016 | 11:00 AM | Sat | Middleboro / Field of Dreams/Braga Complex | Plymouth BU14-1 (Krueger) | Postponed | Middleboro BU14-1 (McKenna) | Postponed |
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| 270001 | 4/9/2016 | 1:00 PM | Sat | Carver / High School | Middleboro BU14-1 (McKenna) | 1 | Carver BU14-1 (Millman) | 0 |
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| 270017 | 4/16/2016 | 11:00 AM | Sat | Middleboro / Field of Dreams/Braga Complex | Hanover BU14-1 (Bristol) | 4 | Middleboro BU14-1 (McKenna) | 0 |
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| 270018 | 4/23/2016 | 1:00 PM | Sat | Middleboro / Field of Dreams/Braga Complex | Duxbury BU14-1 (Simonini) | 7 | Middleboro BU14-1 (McKenna) | 1 |
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| 270028 | 4/30/2016 | 12:30 PM | Sat | Scituate / High School Turf | Middleboro BU14-1 (McKenna) | 1 | Scituate BU14-1 (O'Connor) | 3 |
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| 270023 | 5/7/2016 | 8:30 AM | Sat | Plymouth / Forges Field 2B | Middleboro BU14-1 (McKenna) | 2 | Plymouth BU14-1 (Krueger) | 4 |
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| 270032 | 5/13/2016 | 2:00 PM | Fri | Middleboro / Field of Dreams/Braga Complex | Plymouth BU14-1 (Krueger) | 3 | Middleboro BU14-1 (McKenna) | 1 |
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| 270019 | 5/14/2016 | 1:00 PM | Sat | Middleboro / Field of Dreams/Braga Complex | Carver BU14-1 (Millman) | 1 | Middleboro BU14-1 (McKenna) | 3 |
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| 270014 | 5/21/2016 | 8:00 AM | Sat | Hanover / High School | Middleboro BU14-1 (McKenna) | 1 | Hanover BU14-1 (Bristol) | 3 |
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| 270010 | 5/28/2016 | 10:30 AM | Sat | Duxbury / Coppens Field U10 U12 U14 2 | Middleboro BU14-1 (McKenna) | Forfeit | Duxbury BU14-1 (Simonini) | Win |
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| 270020 | 6/4/2016 | 11:00 AM | Sat | Middleboro / Field of Dreams/Braga Complex | Scituate BU14-1 (O'Connor) | 2 | Middleboro BU14-1 (McKenna) | 2 |
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