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| Tue | May 22 | BU10D3 | Align Health Care Field | 18:30 | Newmarket White Bu10 D3 | | Woodbridge Yellow Bu10 D3 |
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| Tue | May 22 | BU13D2 | Brother Andre A | 19:00 | Markham Gold Bu13 D2 | 3 - 2 | Richmond Hill White Bu13 D2 |
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| Tue | May 22 | GU13D1 | Centennial Park Markham | 19:00 | Markham Black Gu13 D1 | 4 - 0 | Richmond Hill Green Gu13 D1 |
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| Tue | May 22 | BU10D2 | Chancellor Park 1 | 19:00 | Woodbridge Green Bu10 D2 | | Aurora Yellow Bu10 D2 |
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| Tue | May 22 | GU12D2 | Civic Centre (Lake Simcoe) #2 | 19:00 | Lssc Red Devils Gu12 D2 | | Markham Gold Gu12 D2 |
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| Tue | May 22 | BU10D3 | Civic Centre (Lake Simcoe) #6 | 19:00 | Lssc Red Devils Bu10 D3 | | Richmond Hill Black Bu10 D3 |
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| Tue | May 22 | GU13D2 | Civic Centre (Lake Simcoe) #7 | 19:00 | Lssc Red Devils Gu13 D2 | 4 - 2 | North Durham United FC Gu13 D2 |
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| Tue | May 22 | GU12D2 | Clearview Park 9 v 9 | 19:00 | Vaughan T2 Gu12 D2 | | Wssc Gu12 D2 |
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| Tue | May 22 | BU13D1 | Concord Thornhill 1 | 19:00 | Glen Shields Red Bu13 D1 | 5 - 0 | Knsc Red Bu13 D1 |
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| Tue | May 22 | GU13D1 | Dr. Denison Turf - Newmarket | 19:00 | Newmarket Red Gu13 D1 | 0 - 2 | Woodbridge Blue Gu13 D1 |
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| Tue | May 22 | BU10D1 | Freedom Trail Mini | 19:00 | Vaughan T2 Bu10 D1 | | Vaughan T1 Bu10 D1 |
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| Tue | May 22 | BU13D1 | Grovewood Park | 19:00 | Oak Ridges Blue Bu13 D1 | 6 - 2 | Newmarket Red Bu13 D1 |
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| Tue | May 22 | BU10D1 | Guthrie Park West | 19:00 | Whitby Iroquois Bu10 D1 | | Wssc Bu10 D1 |
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| Tue | May 22 | BU10D1 | Harwood Mini 1 | 19:00 | Ajax Red Bu10 D1 | | Pickering Green Bu10 D1 |
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| Tue | May 22 | BU10D3 | Hickson Park | 19:00 | Aurora White Bu10 D3 | | Thornhill Bu10 D3 |
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| Tue | May 22 | BU13D2 | Joe Persechini | 18:00 | Newmarket White Bu13 D2 | 0 - 8 | Vaughan T2 Bu13 D2 |
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| Tue | May 22 | BU10D2 | Joseph Aaron Park | 19:00 | Glen Shields Bu10 D2 | | Knsc Blue Bu10 D2 |
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| Tue | May 22 | GU12D1 | Kleinburg Christian 9v9 #1B | 19:00 | Knsc Red Gu12 D1 | | Aurora Black Gu12 D1 |
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| Tue | May 22 | GU12D1 | Langstaff Park | 19:00 | Vaughan T1 Gu12 D1 | | Markham Black Gu12 D1 |
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| Tue | May 22 | GU13D2 | Maple Leaf Lower | 20:30 | Cavan FC Gu13 D2 | 1 - 7 | East Gwillimbury Gu13 D2 |
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| Tue | May 22 | BU13D2 | McLaren Full | 19:00 | Thornhill Blue Bu13 D2 | 0 - 6 | Woodbridge Strikers EP Bu13 D2 |
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| Tue | May 22 | BU13D1 | McNaughton Turf | 19:00 | Vaughan T1 Bu13 D1 | 3 - 5 | Markham Black Bu13 D1 |
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| Tue | May 22 | GU12D2 | Milliken Mills Complex A | 19:00 | Umsc Gu12 D2 | | Newmarket White Gu12 D2 |
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| Tue | May 22 | BU10D1 | Mitchell Pond Park | 19:00 | Oak Ridges Blue Bu10 D1 | | Woodbridge White Bu10 D1 |
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| Tue | May 22 | GU12D2 | Monticello Park | 19:00 | Richmond Hill Black Gu12 D2 | | Knsc Blue Gu12 D2 |
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| Tue | May 22 | GU13D2 | Morgan Boyle Park | 19:00 | Richmond Hill White Gu13 D2 | 2 - 4 | Oshawa Kicks Gu13 D2 |
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| Tue | May 22 | BU10D1 | Mount Joy Mini East | 19:00 | Markham Black Bu10 D1 | | Knsc Red Bu10 D1 |
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| Tue | May 22 | BU10D2 | Mount Joy Mini North | 19:00 | Markham White Bu10 D2 | | Vaughan T3 Bu10 D2 |
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| Tue | May 22 | GU13D1 | Optimist Park - Aurora | 19:00 | Aurora FC Gu13 D1 | 2 - 4 | Umsc Gu13 D1 |
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| Tue | May 22 | GU12D1 | Pine Farm Park | 19:00 | Oak Ridges Gu12 D1 | | Richmond Hill White Gu12 D1 |
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| Tue | May 22 | GU12D1 | Portage Park | 19:00 | Whitby Iroquois Gu12 D1 | | Barrie FC Blue Gu12 D1 |
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| Tue | May 22 | GU12D1 | Quantztown | 19:00 | Umsc Gu12 D1 | | King City Gu12 D1 |
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| Tue | May 22 | BU10D1 | Richmond Green Junior | 19:00 | Richmond Hill Green Bu10 D1 | | Umsc Bu10 D1 |
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| Tue | May 22 | BU10D2 | Russell Tilt Northeast | 19:00 | Oak Ridges White Bu10 D2 | | Umsc Bu10 D2 |
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| Tue | May 22 | BU10D1 | Sheppards Bush 8 | 19:00 | Aurora Black Bu10 D1 | | Markham Gold Bu10 D1 |
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| Tue | May 22 | BU10D2 | Soccer Nation Field | 18:30 | Newmarket Red Bu10 D2 | | Richmond Hill White Bu10 D2 |
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| Tue | May 22 | BU10D1 | Vaughan Grove Mini 1 | 19:00 | Woodbridge Blue Bu10 D1 | | Barrie FC Blue Bu10 D1 |
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| Tue | May 22 | BU10D2 | Vaughan Grove Mini 2 | 19:00 | Woodbridge Red Bu10 D2 | | Thornhill Red Bu10 D2 |
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| Tue | May 22 | GU12D1 | Wade Gate | 19:00 | Glen Shields Gu12 D1 | | Pickering Green Gu12 D1 |
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| Tue | May 22 | BU10D2 | Wellesley Park | 19:00 | King City Bu10 D2 | | Markham Green Bu10 D2 |
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| Tue | May 22 | BU10D3 | Woodrose Mini Field | 19:00 | Vaughan T4 Bu10 D3 | | East Gwillimbury Bu10 D3 |
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| Wed | May 23 | BU11D2 | Civic Centre (Lake Simcoe) #2 | 19:00 | Lssc Red Devils Bu11 D2 | | Knsc Blue Bu11 D2 |
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| Wed | May 23 | BU11D2 | Clearview Park 9 v 9 | 19:00 | Vaughan T4 Bu11 D2 | | Markham Gold Bu11 D2 |
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| Wed | May 23 | BU11D1 | Darlington Field #5 | 19:00 | Darlington Energy Bu11 D1 | | Ajax Red Bu11 D1 |
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| Wed | May 23 | BU11D1 | Divine Park | 19:00 | Whitby Iroquois Bu11 D1 | | Pickering Green Bu11 D1 |
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| Wed | May 23 | BU15D1 | Franklin Carmichael Park | 19:00 | Thornhill Bu15 D1 | 3 - 3 | Richmond Hill Green Bu15 D1 |
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| Wed | May 23 | GU10D2 | French Royalist Park | 19:00 | Richmond Hill White Gu10 D2 | | Woodbridge White Gu10 D2 |
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| Wed | May 23 | BU15D1 | Grovewood Park | 19:00 | Oak Ridges White Bu15 D1 | 3 - 0 | Newmarket Bu15 D1 |
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| Wed | May 23 | GU10D1 | Guthrie Park West | 19:00 | Whitby Iroquois Gu10 D1 | | Umsc Gu10 D1 |
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| Wed | May 23 | GU10D1 | Joseph Aaron Park | 19:00 | Glen Shields Gu10 D1 | | Markham Black Gu10 D1 |
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| Wed | May 23 | BU11D2 | King Bible Church | 19:00 | King City Bu11 D2 | | Newmarket White Bu11 D2 |
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| Wed | May 23 | BU11D1 | Maple Reservoir 9 v 9 | 19:00 | Vaughan T1 Bu11 D1 | | Knsc Red Bu11 D1 |
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| Wed | May 23 | BU11D2 | McClure Park | 19:00 | Woodbridge Red Bu11 D2 | | East Gwillimbury Bu11 D2 |
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| Wed | May 23 | BU15D1 | McNaughton Turf | 21:00 | Vaughan T1 Bu15 D1 | 6 - 1 | Aurora FC Bu15 D1 |
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| Wed | May 23 | BU11D2 | Milliken Mills Complex A | 19:00 | Umsc Strikers Bu11 D2 | | Umsc Bu11 D2 |
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| Wed | May 23 | GU15D1 | Milliken Mills Complex E | 19:00 | Umsc Gu15 D1 | 4 - 0 | Aurora FC Gu15 D1 |
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| Wed | May 23 | GU15D1 | Mount Albert Lions #2 | 21:00 | East Gwillimbury Gu15 D1 | 0 - 0 | Innisfil Stampeders Gu15 D1 |
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| Wed | May 23 | GU10D2 | Mount Albert Lions Mini #3 | 19:00 | East Gwillimbury Gu10 D2 | | Newmarket Gu10 D2 |
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| Wed | May 23 | GU10D2 | Mount Joy Mini North | 19:00 | Markham White Gu10 D2 | | Vaughan T2 Gu10 D2 |
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| Wed | May 23 | GU10D1 | Mount Joy Mini West | 19:00 | Markham Gold Gu10 D1 | | Vaughan T1 Gu10 D1 |
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| Wed | May 23 | BU11D2 | Pine Farm Park | 19:00 | Oak Ridges White Bu11 D2 | | Newmarket Red Bu11 D2 |
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| Wed | May 23 | BU11D1 | Quantztown | 19:00 | Umsc Bu11 D1 | | Oak Ridges Blue Bu11 D1 |
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| Wed | May 23 | GU10D1 | Richmond Green Junior | 19:00 | Richmond Hill Green Gu10 D1 | | Oak Ridges Gu10 D1 |
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| Wed | May 23 | BU11D2 | Sheppards Bush 10 | 19:00 | Aurora Yellow Bu11 D2 | | Vaughan T3 Bu11 D2 |
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| Wed | May 23 | GU10D2 | Sheppards Bush 8 | 19:00 | Aurora FC Gu10 D2 | | Wssc Gu10 D2 |
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| Wed | May 23 | BU11D1 | Sheppards Bush 9 | 19:00 | Aurora Black Bu11 D1 | | Vaughan T2 Bu11 D1 |
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| Wed | May 23 | BU15D1 | St. Jean de Brebeuf | 19:00 | Woodbridge Red Bu15 D1 | 2 - 2 | Bradford Eagles Bu15 D1 |
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| Wed | May 23 | BU15D1 | St. Joan of Arc - Turf | 19:00 | Vaughan T2 Bu15 D1 | 3 - 2 | Lssc 2 Red Devils Bu15 D1 |
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| Wed | May 23 | GU10D1 | Vaughan Grove Mini 1 | 19:00 | Woodbridge Blue Gu10 D1 | | Oshawa Kicks Red Gu10 D1 |
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| Wed | May 23 | GU15D1 | Verstraten Park | 21:00 | Barrie FC Gu15 D1 | 6 - 0 | Lssc Red Devils Gu15 D1 |
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| Wed | May 23 | BU11D2 | Wade Gate | 19:00 | Glen Shields Bu11 D2 | | Richmond Hill Green Bu11 D2 |
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| Wed | May 23 | BU11D1 | Woodbridge College | 19:00 | Woodbridge White Bu11 D1 | | Woodbridge Blue Bu11 D1 |
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| Thu | May 24 | BU14D2 | Berczy Park Centre | 19:00 | Umsc Bu14 D2 | 2 - 4 | Oak Ridges Blue Bu14 D2 |
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| Thu | May 24 | BU9D1 | Bridle Park | 19:00 | Oshawa Kicks Red Bu9 D1 | | Woodbridge White Bu9 D1 |
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| Thu | May 24 | GU16D1 | Brother Andre A | 21:00 | Markham Black Gu16 D1 | 0 - 3 | Lssc Red Devils Gu16 D1 |
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| Thu | May 24 | BU14D1 | Brother Andre B | 19:00 | Markham Black Bu14 D1 | 0 - 8 | Vaughan T1 Bu14 D1 |
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| Thu | May 24 | GU11D2 | Civic Centre (Lake Simcoe) #2 | 19:00 | Lssc Red Devils Gu11 D2 | | Markham Gold Gu11 D2 |
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| Thu | May 24 | GU16D1 | Concord Thornhill 1 | 21:00 | Glen Shields Epic Gu16 D1 | 3 - 0 | Vaughan T1 Gu16 D1 |
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| Thu | May 24 | BU9D2 | Freedom Trail Mini | 19:00 | Vaughan T2 Bu9 D2 | | Markham White Bu9 D2 |
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| Thu | May 24 | GU16D1 | Gostick Park #1 | 21:00 | Bracebridge Storm Gu16 D1 | 1 - 9 | Newmarket Gu16 D1 |
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| Thu | May 24 | BU9D1 | Harwood Mini 1 | 19:00 | Ajax Red Bu9 D1 | | Oak Ridges Blue Bu9 D1 |
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| Thu | May 24 | GU16D1 | Henderson Park West | 21:00 | Bradford Eagles Gu16 D1 | 7 - 2 | King City Gu16 D1 |
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| Thu | May 24 | BU11D1 | King Bible Church | 19:00 | King City United Bu11 D1 | | Markham Black Bu11 D1 |
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| Thu | May 24 | GU11D1 | Kinsmen Park 1 - Pickering | 19:00 | Pickering Green Gu11 D1 | | Whitby Iroquois Gu11 D1 |
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| Thu | May 24 | BU9D3 | Mitchell Pond Park | 19:00 | Oak Ridges White Bu9 D3 | | Newmarket White Bu9 D3 |
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| Thu | May 24 | GU11D2 | Monticello Park | 19:00 | Richmond Hill White Gu11 D2 | | Aurora Yellow Gu11 D2 |
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| Thu | May 24 | BU9D2 | Mount Joy Mini North | 19:00 | Markham Green Bu9 D2 | | Newmarket Red Bu9 D2 |
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| Thu | May 24 | BU9D1 | Mount Joy Mini West | 19:00 | Markham Gold Bu9 D1 | | Vaughan T1 Bu9 D1 |
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| Thu | May 24 | BU14D1 | Optimist Park - Aurora | 19:00 | Aurora FC Bu14 D1 | 3 - 1 | Oak Ridges White Bu14 D1 |
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| Thu | May 24 | GU11D1 | Quantztown | 19:00 | Umsc Gu11 D1 | | Oak Ridges Gu11 D1 |
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| Thu | May 24 | GU11D1 | Randall Park | 19:00 | Markham Black Gu11 D1 | | Wssc Gu11 D1 |
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| Thu | May 24 | BU14D1 | Ray Twinney #1 | 19:00 | Newmarket United A Bu14 D1 | 4 - 4 | Woodbridge Strikers RB Bu14 D1 |
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| Thu | May 24 | GU11D1 | Richardson Park #7 | 19:00 | Newmarket Red Gu11 D1 | | Oshawa Kicks Red Gu11 D1 |
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| Thu | May 24 | BU14D1 | Richmond Green East | 19:00 | Richmond Hill Green Bu14 D1 | 10 - 0 | King City Bu14 D1 |
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| Thu | May 24 | BU9D1 | Richmond Green Junior | 19:00 | Richmond Hill Green Bu9 D1 | | Markham Black Bu9 D1 |
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| Thu | May 24 | BU14D2 | Richvale Park Sr. | 19:00 | Richmond Hill White Bu14 D2 | 2 - 2 | Thornhill Bu14 D2 |
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| Thu | May 24 | GU11D2 | Ross Complex | 19:00 | East Gwillimbury Gu11 D2 | | Umsc Gu11 D2 |
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| Thu | May 24 | GU11D1 | Sheppards Bush 10 | 19:00 | Aurora Black Gu11 D1 | | Woodbridge Blue Gu11 D1 |
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| Thu | May 24 | BU9D1 | Sheppards Bush 8 | 19:00 | Aurora Black Bu9 D1 | | Glen Shields Bu9 D1 |
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| Thu | May 24 | BU9D1 | Vaughan Grove Mini 1 | 19:00 | Woodbridge Blue Bu9 D1 | | Whitby Iroquois Bu9 D1 |
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| Thu | May 24 | BU9D3 | Vaughan Grove Mini 2 | 19:00 | Woodbridge Green Bu9 D3 | | Lssc Red Devils Bu9 D3 |
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| Thu | May 24 | BU9D2 | Village Park Mini 2 | 19:00 | Umsc Bu9 D2 | | Aurora Yellow Bu9 D2 |
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| Thu | May 24 | GU14D1 | Villanova South | 19:00 | King City Gu14 D1 | 2 - 2 | Umsc Gu14 D1 |
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| Thu | May 24 | BU9D2 | Wellesley Park | 19:00 | King City Bu9 D2 | | Thornhill Bu9 D2 |
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| Thu | May 24 | GU11D2 | Woodbridge College | 19:00 | Woodbridge White Gu11 D2 | | King City Gu11 D2 |
