| 280021 | 4/2/2016 | 11:00 AM | Sat | Norwell / Stadium Turf | Pembroke BU14-2 (Halloran) | 0 | Norwell BU14-2 (Ingargiola) | 2 |
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| 280001 | 4/9/2016 | 10:45 AM | Sat | Cohasset / High School-Varsity | Pembroke BU14-2 (Halloran) | 2 | Cohasset BU14-2 (DeVries) | 0 |
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| 280026 | 4/16/2016 | 11:00 AM | Sat | Pembroke / Hobomock Field 1B | Marshfield BU14-2 (Burns) | 1 | Pembroke BU14-2 (Halloran) | 2 |
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| 280027 | 4/23/2016 | 12:30 PM | Sat | Pembroke / Pembroke High School | Kingston BU14-2 (Garcia) | 0 | Pembroke BU14-2 (Halloran) | 4 |
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| 280008 | 4/30/2016 | 12:00 PM | Sat | Hingham / Union R | Pembroke BU14-2 (Halloran) | 6 | Hingham BU14-2 (Sharp) | 2 |
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| 280036 | 5/7/2016 | 11:30 AM | Sat | Scituate / High School Turf | Pembroke BU14-2 (Halloran) | 0 | Scituate BU14-3 (Maher) | 0 |
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| 280028 | 5/14/2016 | 3:30 PM | Sat | Pembroke / Pembroke High School | Scituate BU14-2 (Fogarty) | 4 | Pembroke BU14-2 (Halloran) | 1 |
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| 280029 | 5/21/2016 | 12:30 PM | Sat | Pembroke / Pembroke High School | Cohasset BU14-2 (DeVries) | Forfeit | Pembroke BU14-2 (Halloran) | Win |
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| 280015 | 6/2/2016 | 6:00 PM | Thu | Kingston / Pottle Street | Pembroke BU14-2 (Halloran) | 1 | Kingston BU14-2 (Garcia) | 0 |
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| 280030 | 6/4/2016 | 5:00 PM | Sat | Pembroke / Pembroke High School | Scituate BU14-3 (Maher) | 0 | Pembroke BU14-2 (Halloran) | 2 |
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