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| Tue | May 21 | GU13D1 | Audrey Sanderson (Silken Laumann) | 19:00 | Newmarket United Gu13 D1 | 0 - 2 | Knsc Lions Gu13 D1 |
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| Tue | May 21 | BU10GR | Bethedsa Mini A | 19:00 | Wssc Bu10 Green | | Woodbridge Green Bu10 Green |
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| Tue | May 21 | GU13D1 | Civic Centre (Lake Simcoe) #10 | 19:00 | Lssc Red Devils Gu13 D1 | 4 - 0 | Wssc Gu13 D1 |
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| Tue | May 21 | GU13D1 | Fisher Field #1 | 19:00 | Collingwood Gu13 D1 | 3 - 2 | Richmond Hill Gu13 D1 |
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| Tue | May 21 | BU10GY | Freedom Trail Mini | 19:00 | Vaughan Azzurri T2 Bu10 Grey | | Barrie White FC Bu10 Grey |
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| Tue | May 21 | BU10GR | French Royalist Park | 19:00 | Richmond Hill White Bu10 Green | | Markham Lightning Orange Bu10 Green |
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| Tue | May 21 | BU10GY | Hickson Park | 19:00 | Aurora FC Yellow Bu10 Grey | | Lssc Red Devils Bu10 Grey |
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| Tue | May 21 | BU10GY | Huntington Park Mini West | 19:00 | Thornhill Bu10 Grey | | Vaughan Azzurri T3 Bu10 Grey |
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| Tue | May 21 | GU12GY | Maple Reservoir 9 v 9 | 19:00 | Vaughan Azzurri T3 Gu12 Grey | | Aurora Yellow Gu12 Grey |
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| Tue | May 21 | GU12BL | McClure Park | 19:00 | Woodbridge White Gu12 Blue | | King City Royals Gu12 Blue |
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| Tue | May 21 | BU10BL | McLaren Mini | 19:00 | Thornhill Maccabi Canada Bu10 Blue | | King City Royals Bu10 Blue |
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| Tue | May 21 | GU12BL | Milani Field | 19:00 | Woodbridge Red Gu12 Blue | | Wssc Gu12 Blue |
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| Tue | May 21 | BU10GR | Mitchell Pond Park | 19:00 | Oak Ridges White Bu10 Green | | Newmarket Blue Bu10 Green |
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| Tue | May 21 | GU12BL | Monticello Park | 19:00 | Richmond Hill Green Gu12 Blue | | Barrie FC Gu12 Blue |
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| Tue | May 21 | BU10BL | Mount Joy Mini East | 19:00 | Markham Lightning White Bu10 Blue | | Barrie Blue FC Bu10 Blue |
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| Tue | May 21 | BU10GY | Mount Joy Mini West | 19:00 | Markham Lightning Green Bu10 Grey | | Newmarket White Bu10 Grey |
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| Tue | May 21 | GU12GY | Quantztown | 19:00 | Umsc White Gu12 Grey | | Newmarket White Gu12 Grey |
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| Tue | May 21 | BU10BL | Richmond Green Junior | 19:00 | Richmond Hill Green Bu10 Blue | | GFC White Bu10 Blue |
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| Tue | May 21 | BU10BK | Sheppards Bush 8 | 19:00 | Aurora Black Bu10 Black | | Woodbridge Blue Bu10 Black |
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| Tue | May 21 | BU10BK | Sonoma South | 19:00 | Knsc Lions Blue Bu10 Black | | Vaughan Azzurri T1 Bu10 Black |
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| Tue | May 21 | BU10BK | Trio Sportsplex #1 | 18:30 | GFC Black Bu10 Black | | Markham Lightning Black Bu10 Black |
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| Tue | May 21 | BU10BK | Vaughan Grove Mini 1 | 19:00 | Woodbridge White Bu10 Black | | Oak Ridges Blue Bu10 Black |
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| Tue | May 21 | BU10BL | Vaughan Grove Mini 2 | 19:00 | Woodbridge Red Bu10 Blue | | Knsc Lions Red Bu10 Blue |
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| Tue | May 21 | BU10BK | Village Park Mini 2 | 19:00 | Umsc Red Bu10 Black | | Markham Lightning Gold Bu10 Black |
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| Tue | May 21 | GU12BL | Wade Gate | 19:00 | Vaughan Azzurri T2 Gu12 Blue | | Oak Ridges Gu12 Blue |
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| Tue | May 21 | GU12GY | William Harrison Park | 19:00 | Richmond Hill White Gu12 Grey | | Lssc Red Devils Gu12 Grey |
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| Wed | May 22 | BU15D1 | Ballantrae Field A | 19:00 | Wssc Mustangs Bu15 D1 | 2 - 2 | Vaughan Azzurri T1 Bu15 D1 |
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| Wed | May 22 | BU18D1 | Barrie Sports Complex #4 | 19:00 | Barrie FC Bu18 D1 | 3 - 1 | Barrie FC Bu17 D1 |
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| Wed | May 22 | BU11GR | Bayview Reservoir (Thornlea S.S) | 19:00 | Thornhill Red Bu11 Green | | Lssc Red Devils Bu11 Green |
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| Wed | May 22 | BU18D1 | Bethedsa Full (Lit) | 21:00 | Wssc Mustangs Bu18 | 5 - 0 | Markham Lightning Bu18 |
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| Wed | May 22 | GU10GY | Bethedsa Mini A | 19:00 | Wssc Gu10 Grey | | Woodbridge White Gu10 Grey |
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| Wed | May 22 | BU18D1 | Bishops Cross | 19:00 | Thornhill Red Bu17 | 0 - 3 | Richmond Hill White Bu17 |
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| Wed | May 22 | GU10BL | Civic Centre (Lake Simcoe) #10 | 19:00 | Lssc Red Devils Gu10 Blue | | Barrie FC Gu10 Blue |
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| Wed | May 22 | GU15D1 | Crosby Park Richmond Hill | 19:00 | Richmond Hill Gu15 D1 | 0 - 3 | Barrie FC Gu15 D1 |
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| Wed | May 22 | BU18D1 | Eastgate #1 | 21:00 | Peterborough City Bu18 D1 | 1 - 3 | Bradford Wolves Bu17 D1 |
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| Wed | May 22 | BU15D1 | Grovewood Park | 21:00 | Oak Ridges Blue Bu15 D1 | 4 - 2 | Newmarket United B Bu15 D1 |
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| Wed | May 22 | BU11GY | James Edward Park | 19:00 | Markham Lightning White Bu11 Grey | | Knsc Lions Blue Bu11 Grey |
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| Wed | May 22 | BU18D1 | Kleinburg Christian 11v11 #2 | 19:00 | Knsc Lions Bu17 | 6 - 0 | Aurora FC Bu17 |
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| Wed | May 22 | BU11BK | Kleinburg Christian 9v9 #1A | 19:00 | Knsc Lions Red Bu11 Black | | Markham Lightning Black Bu11 Black |
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| Wed | May 22 | BU11GR | Maple Reservoir 9 v 9 | 19:00 | Vaughan Azzurri T4 Bu11 Green | | Oak Ridges White Bu11 Green |
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| Wed | May 22 | BU11BL | McClure Park | 19:00 | Woodbridge Red Bu11 Blue | | King City Royals Bu11 Blue |
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| Wed | May 22 | GU15D1 | McNaughton Turf | 19:00 | Vaughan Azzurri Gu15 D1 | 4 - 3 | Knsc Lions Gu15 D1 |
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| Wed | May 22 | BU11BK | Milani Field | 19:00 | Woodbridge Blue Bu11 Black | | Woodbridge White Bu11 Black |
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| Wed | May 22 | BU11BK | Milliken Mills Complex 3 | 19:00 | Umsc2 Bu11 Black | | Aurora FC Black Bu11 Black |
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| Wed | May 22 | GU15D1 | Milliken Mills Complex E | 19:00 | Umsc White Gu15 D1 | 0 - 4 | King City Royals Gu15 D1 |
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| Wed | May 22 | GU10BK | Mitchell Pond Park | 19:00 | Oak Ridges Gu10 Black | | Markham Lightning Gold Gu10 Black |
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| Wed | May 22 | BU11GY | Monticello Park | 19:00 | Richmond Hill Green Bu11 Grey | | Thornhill Blue Bu11 Grey |
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| Wed | May 22 | GU10BK | Mount Joy Mini North | 19:00 | Markham Lightning Black Gu10 Black | | Woodbridge Blue Gu10 Black |
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| Wed | May 22 | GU10BL | Mount Joy Mini West | 19:00 | Markham Lightning White Gu10 Blue | | Aurora FC Yellow Gu10 Blue |
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| Wed | May 22 | BU11BL | Nobleton Junior School | 19:00 | Barrie Blue FC Bu11 Blue | | Vaughan Azzurri T3 Bu11 Blue |
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| Wed | May 22 | BU11BL | Pine Farm Park | 19:00 | Oak Ridges Blue Bu11 Blue | | Wssc Bu11 Blue |
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| Wed | May 22 | BU11BL | Quantztown | 19:00 | Umsc Red Bu11 Blue | | Newmarket Red Bu11 Blue |
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| Wed | May 22 | BU11BK | Randall Park | 19:00 | Markham Lightning Gold Bu11 Black | | Vaughan Azzurri T2 Bu11 Black |
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| Wed | May 22 | GU10GY | Richmond Green Junior | 19:00 | Richmond Hill Gu10 Grey | | King City Royals Gu10 Grey |
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| Wed | May 22 | GU10BK | Sheppards Bush 8 | 19:00 | Aurora FC Black Gu10 Black | | Vaughan T1 Gu10 Blck |
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| Wed | May 22 | BU11GY | Sheppards Bush 9 | 19:00 | Aurora Yellow Bu11 Grey | | Umsc White Bu11 Grey |
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| Wed | May 22 | BU15D1 | St. Robs C.H.S. | 19:00 | Thornhill Bu15 D1 | 1 - 2 | Knsc Lions Bu15 D1 |
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| Wed | May 22 | BU11BK | Wade Gate | 19:00 | Vaughan Azzurri T1 Bu11 Black | | GFC Black Bu11 Black |
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| Wed | May 22 | GU10BL | Woodrose Mini Field | 19:00 | Vaughan Azzurri T2 Gu10 Blue | | Knsc Lions Gu10 Blue |
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| Thu | May 23 | GU16D1 | Anchor Park | 19:00 | East Gwillimbury Talons 03 Girls | 6 - 2 | Markham Lightning Gu16 D1 |
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| Thu | May 23 | BU9GY | Armstrong Mini | 19:00 | Markham Lightning Green Bu9 Grey | | Richmond Hill Silver Bu9 Grey |
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| Thu | May 23 | BU9GY | Autumn Grove Park | 19:00 | Richmond Hill Black Bu9 Grey | | Woodbridge Green Bu9 Grey |
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| Thu | May 23 | BU14D2 | Ballantrae Field A | 19:00 | Wssc Mustangs Bu14 D2 | 4 - 0 | Thornhill Blue Bu14 D2 |
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| Thu | May 23 | BU9GY | Bethedsa Mini A | 19:00 | Wssc Bu9 Grey | | King City Royals Bu9 Grey |
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| Thu | May 23 | BU9GR | Civic Centre (Lake Simcoe) #10 | 19:00 | Lssc Red Devils Bu9 Green | | Newmarket White Bu9 Green |
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| Thu | May 23 | BU14D1 | Concord Thornhill 1 | 19:30 | Glen Shields FC Bu14 D1 | 0 - 1 | Woodbridge Bu14 D1 |
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| Thu | May 23 | GU15D1 | Fisher Field #1 | 21:00 | Collingwood Gu15 D1 | 3 - 0 | Newmarket United Gu15 D1 |
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| Thu | May 23 | BU9BK | Freedom Trail Mini | 19:00 | Vaughan Azzurri T1 Bu9 Black | | Woodbridge White Bu9 Black |
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| Thu | May 23 | BU9BL | French Royalist Park | 19:00 | Richmond Hill White Bu9 Blue | | Vaughan Azzurri T2 Bu9 Blue |
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| Thu | May 23 | BU9BL | Haskett #4 | 19:00 | Barrie Blue FC Bu9 Blue | | Aurora Yellow Bu9 Blue |
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| Thu | May 23 | BU9GY | Huntington Park Mini West | 19:00 | Thornhill Bu9 Grey | | Umsc White Bu9 Grey |
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| Thu | May 23 | GU11BL | King Bible Church | 19:00 | King City Royals Gu11 Blue | | Vaughan Azzurri T2 Gu11 Blue |
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| Thu | May 23 | GU11BL | McClure Park | 19:00 | Woodbridge White Gu11 Blue | | GFC Black Gu11 Blue |
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| Thu | May 23 | GU11BK | Milani Field | 19:00 | Woodbridge Blue Gu11 Black | | Markham Lightning Black Gu11 Black |
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| Thu | May 23 | GU16D1 | Milliken Mills Complex E | 21:00 | Umsc Gu16 D1 | 2 - 1 | Newmarket United Gu16 D1 |
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| Thu | May 23 | BU9GR | Mitchell Pond Park | 19:00 | Oak Ridges Bu9 Green | | Thornhill Thunder - FSA Bu9 Green |
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| Thu | May 23 | BU9BK | Mount Joy Mini East | 19:00 | Markham Lightning Gold Bu9 Black | | Aurora FC Black Bu9 Black |
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| Thu | May 23 | BU9BK | Mount Joy Mini North | 19:00 | Markham Lightning Black Bu9 Black | | Richmond Hill Green Bu9 Black |
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| Thu | May 23 | BU9BL | Mount Joy Mini West | 19:00 | Markham Lightning White Bu9 Blue | | Woodbridge Red Bu9 Blue |
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| Thu | May 23 | GU16D1 | Optimist Park - Aurora | 19:00 | Aurora FC Gu16 D1 | 5 - 2 | King City United Gu16 D1 |
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| Thu | May 23 | BU9GR | Pheasant Hallow Mini | 19:00 | Vaughan T4 Bu9 Green | | Knsc Lions Bu9 Green |
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| Thu | May 23 | GU11BK | Pine Farm Park | 19:00 | Oak Ridges Gu11 Black | | Richmond Hill Gu11 Black |
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| Thu | May 23 | GU11BL | Quantztown | 19:00 | Umsc Red Gu11 Blue | | Newmarket United Gu11 Blue |
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| Thu | May 23 | BU14D1 | Richardson Park #1 | 19:00 | Newmarket United Bu14 D1 | 0 - 6 | Thornhill Red Bu14 D1 |
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| Thu | May 23 | BU14D1 | Richmond Green East | 19:00 | Richmond Hill Bu14 D1 | 1 - 6 | Vaughan Azzurri T1 Bu14 D1 |
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| Thu | May 23 | GU11BL | Ross Complex | 19:00 | East Gwillimbury Talons 08 Girls | | Aurora FC Yellow Gu11 Blue |
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| Thu | May 23 | GU11BK | Sheppards Bush 9 | 19:00 | Aurora FC Black Gu11 Black | | Markham Lightning Gold Gu11 Black |
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| Thu | May 23 | BU14D2 | Sonoma Turf | 19:00 | Knsc Lions Blue Bu14 D2 | 2 - 2 | Oak Ridges White Bu14 D2 |
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| Thu | May 23 | BU9GY | Trio Sportsplex #1 | 18:00 | Glen Shields Grey Bu9 Grey | | Vaughan Azzurri T3 Bu9 Grey |
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| Thu | May 23 | BU9BK | Vaughan Grove Mini 1 | 19:00 | Woodbridge Blue Bu9 Black | | Newmarket Red Bu9 Black |
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| Thu | May 23 | BU9BK | Village Park Mini 1 | 19:00 | Umsc Red Bu9 Black | | GFC Black Bu9 Black |
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| Sat | May 25 | BU12BK | King Bible Church | 11:00 | King City United Bu12 Black | | Woodbridge White Bu12 Black |
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| Sat | May 25 | BU12BK | Langstaff Park | 11:00 | Vaughan Azzurri T2 Bu12 Black | | Vaughan Azzurri T1 Bu12 Black |
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| Sat | May 25 | BU12BK | Milani Field | 11:00 | Woodbridge Blue Bu12 Black | | GFC Black Bu12 Black |
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| Sat | May 25 | GU12BK | Quantztown | 11:00 | Umsc Red Gu12 Black | | Woodbridge Blue Gu12 Black |
