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| Mon | May 19 | U15GIM | Darlington Field #4 | 19:00 | Darlington Energy U15G IM | 1 - 4 | Cherry Beach U15G IM |
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| Mon | May 19 | U15GIM | Iroquois Park | 19:00 | Whitby FC U15G IM | 1 - 1 | Toronto High Park U15G IM |
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| Mon | May 19 | U14G | Wilson Field Lower #1 | 19:00 | Kawartha Inferno U14G | 5 - 0 | Peterborough City White U14G |
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| Tue | May 20 | U13G | Beavermead #1 | 19:00 | Peterborough City White U13G | 3 - 1 | Northumberland U13G |
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| Tue | May 20 | U15B | Beavermead #3 | 19:00 | Peterborough City White U15B | 3 - 3 | Peterborough City Black U15B |
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| Tue | May 20 | U11GT2 | CCC 1 | 19:00 | Northumberland U11G T2 | | Darlington Rush U11G T2 |
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| Tue | May 20 | U10GT1 | Chris Graham 2 | 19:00 | Pickering FC Black U10G T1 | | Darlington Energy U10G T1 |
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| Tue | May 20 | U16BIM | Civic Field #3 (Durham) | 21:00 | Oshawa Kicks Red U16B IM | 4 - 1 | Whitby FC U16B IM |
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| Tue | May 20 | U10GT1 | Civic Field House C | 19:00 | FC Durham U10G T1 | | Whitby FC Blue U10G T1 |
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| Tue | May 20 | U15B | Consumers Field South | 19:00 | Whitby FC U15B | 3 - 1 | Oshawa Turul Fury U15B |
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| Tue | May 20 | U13G | Darlington Field #3 | 19:00 | Darlington Rush U13G | 0 - 6 | Peterborough City Blue U13G |
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| Tue | May 20 | U11GT1 | Darlington Field #5 | 19:00 | Darlington Energy U11G T1 | | Pickering FC Black U11G T1 |
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| Tue | May 20 | U16BIM | Donegan Park | 19:00 | Northumberland U16B IM | 3 - 1 | DeRo TFC U16B IM |
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| Tue | May 20 | U16BIM | Fleming PYSC East Turf | 20:00 | Peterborough City U16B IM | 2 - 2 | Oshawa Turul U16B IM |
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| Tue | May 20 | U8G | Gordon #5 | 18:00 | Whitby FC Blue U8G | | Pickering FC White U8G |
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| Tue | May 20 | U8G | Gordon #5 | 19:00 | Whitby FC White U8G | | Darlington Energy U8G |
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| Tue | May 20 | U10GT1 | Guthrie Park West | 19:00 | Whitby FC Yellow U10G T1 | | Oshawa Kicks Red U10G T1 |
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| Tue | May 20 | U10GT2 | James Cockburn #3 | 19:00 | Northumberland Blue U10GT2 | | Cavan FC Red U10G T2 |
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| Tue | May 20 | U11GT2 | Kinsmen Park 1 - Pickering | 19:00 | Pickering FC Grey U11G T2 | | Whitby FC Yellow U11G T2 |
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| Tue | May 20 | U8G | Kinsmen Park 4 - #1 | 19:00 | Pickering FC Grey U8G | | Whitby FC Yellow U8G |
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| Tue | May 20 | U13G | Lakeview Park West | 18:30 | Oshawa Kicks U13G | 14 - 0 | Cavan FC U13G |
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| Tue | May 20 | U11GT2 | Laval Park | 19:00 | Oshawa Kicks White U11G T2 | | NDUFC U11G T2 |
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| Tue | May 20 | U15B | Lions Park 2 Cobourg | 19:00 | Northumberland U15B | 1 - 2 | Darlington Rush U15B |
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| Tue | May 20 | U12GT1 | Maple Leaf Lower | 19:30 | Cavan FC Red U12G T1 | | Whitby Blue U12G T1 |
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| Tue | May 20 | U10GT2 | Maple Leaf Lower North | 18:30 | Cavan FC Black U10G T2 | | Northumberland Black U10G T2 |
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| Tue | May 20 | U11GT2 | Maple Leaf Upper | 18:30 | Cavan FC Black U11G T2 | | Peterborough City U11G T2 |
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| Tue | May 20 | U10GT2 | Margate Park | 19:00 | Oshawa Kicks White U10G T2 | | Pickering FC Grey U10G T2 |
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| Tue | May 20 | U15B | North Oshawa Park | 18:30 | Oshawa Kicks White U16B | 6 - 3 | Pickering FC U16B |
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| Tue | May 20 | U11GT1 | Portage Park | 19:00 | Whitby FC Blue U11G T1 | | FC Durham U11G T1 |
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| Tue | May 20 | U8G | Southmead Park #3 | 19:00 | Oshawa Kicks Red U8G | | Oshawa Kicks White U8G |
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| Tue | May 20 | U11GT1 | Terry Fox Park | 19:00 | Oshawa Kicks Red U11G T1 | | Cavan FC Red U11G T1 |
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| Tue | May 20 | U8G | Uxbridge Field #1 | 19:00 | NDUFC U8G | | Pickering FC Black U8G |
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| Tue | May 20 | U10GT2 | Whitby Optimist Park | 19:00 | Whitby FC White U10G T2 | | NDUFC U10G T2 |
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| Tue | May 20 | U15B | Wilson Field Upper #3 | 19:00 | Kawartha Inferno U16B | 3 - 5 | Pickering FC U15B |
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| Tue | May 20 | U18G | Wilson Field Upper #3 | 21:00 | Kawartha Inferno U18G | 8 - 0 | Peterborough City U17G |
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| Wed | May 21 | U18G | Alexandra Park | 19:00 | Oshawa Kicks U18G | 8 - 1 | Cavan FC U18G |
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| Wed | May 21 | U9BT2 | Beavermead #5 | 19:00 | Peterborough City White U9B T2 | | Whitby FC Navy U9B T2 |
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| Wed | May 21 | U9B T1 | Beavermead #6 | 19:00 | Peterborough City Blue U9B T1 | | Pickering FC Black U9B T1 |
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| Wed | May 21 | U11BT2 | CCC 2 | 19:00 | Northumberland Black U11B T2 | | Peterborough City Blue U11BT2 |
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| Wed | May 21 | U9BT2 | Chris Graham 1 | 19:00 | Pickering FC White U9B T2 | | Whitby FC Silver U9B T2 |
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| Wed | May 21 | U11BT1 | Civic Field #2 (Durham) | 19:00 | FC Durham Blue U11B T1 | | Darlington Energy U11B T1 |
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| Wed | May 21 | U9B T1 | Civic Field House C | 19:00 | FC Durham U9B T1 | | Pickering FC Grey U9B T1 |
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| Wed | May 21 | U14B | Connaught Park (Oshawa) | 19:00 | Oshawa Turul White U14B | 9 - 3 | Kawartha Inferno U14B |
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| Wed | May 21 | U18G | Consumers Field South | 21:00 | Whitby FC U17G | 3 - 3 | Belleville U18G |
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| Wed | May 21 | U9BT2 | Cullen Field | 19:00 | Whitby FC White U9B T2 | | Kawartha Inferno Black U9B T2 |
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| Wed | May 21 | U9BT2 | Darlington Field #2 | 19:00 | Darlington Rush U9B T2 | | Northumberland Black U9B T2 |
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| Wed | May 21 | U14B | Darlington Field #4 | 19:00 | Darlington Rush U14B | 3 - 1 | Oshawa Turul Green U14B |
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| Wed | May 21 | U18G | Eastgate #1 | 21:00 | Peterborough City U18G | 1 - 3 | MFA U17G |
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| Wed | May 21 | U14B | Eastgate #2 | 19:00 | Peterborough City Blue U14B | 3 - 0 | Peterborough City White U14B |
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| Wed | May 21 | U11BT2 | Eastgate #3 | 19:00 | Peterborough City White U11B T2 | | NDUFC U11B T2 |
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| Wed | May 21 | U11BT1 | Greenhill Park | 19:00 | Oshawa Turul Titans U11B T1 | | Whitby FC Yellow U11B T1 |
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| Wed | May 21 | U9B T1 | Guthrie Park West | 19:00 | Whitby FC Blue U9B T1 | | DeRo TFC Red U9B T1 |
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| Wed | May 21 | U14BIM | Iroquois Park | 19:00 | Whitby FC U14B IM | 6 - 0 | MFA U14B IM |
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| Wed | May 21 | U18G | Iroquois Park | 21:00 | Whitby FC U18G | 0 - 1 | NDUFC U18G |
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| Wed | May 21 | U9BT2 | James Cockburn #4 | 19:00 | Northumberland Blue U9B T2 | | Darlington Dash U9B T2 |
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| Wed | May 21 | U18G | Lake Vista Park | 19:00 | Oshawa Kicks U17G | 0 - 5 | Quinte West Wolverines U18G |
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| Wed | May 21 | U9BT2 | Maple Leaf Lower North | 18:30 | Cavan FC Black U9B T2 | | Peterborough City Black U9B T2 |
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| Wed | May 21 | U11BT2 | Maple Leaf Upper | 18:30 | Cavan FC Red U11B T2 | | Darlington Rush U11B T2 |
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| Wed | May 21 | U9BT2 | Margate Park | 19:00 | Oshawa Kicks White U9B T2 | | Oshawa Turul White U9B T2 |
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| Wed | May 21 | U11BT1 | McLaughlin Park | 19:00 | Oshawa Turul Azzurri U11B T1 | | Northumberland Blue U11B T1 |
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| Wed | May 21 | U11BT1 | Memorial Park - Ajax | 18:00 | DeRo TFC Red U11B T1 | | FC Durham Black U11B T1 |
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| Wed | May 21 | U11BT2 | Memorial Park - Ajax | 19:15 | DeRo TFC Black U11B T2 | | Oshawa Kicks White U11BT2 |
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| Wed | May 21 | U9BT2 | Optimist Park 4 Kawartha Lakes | 19:00 | Kawartha Inferno Red U9B T2 | | NDUFC U9B T2 |
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| Wed | May 21 | U14B | Peel Park | 20:00 | Whitby FC U14B | 4 - 0 | Northumberland U14B |
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| Wed | May 21 | U9B T1 | Pine Crest Park | 19:00 | Oshawa Kicks Red U9B T1 | | Darlington Energy U9B T1 |
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| Wed | May 21 | U11BT1 | Portage Park | 19:00 | Whitby FC Blue U11B T1 | | Oshawa Kicks Red U11B T1 |
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| Wed | May 21 | U14BIM | South Courtice Arena | 19:00 | DeRo TFC U14B IM | 3 - 1 | Oshawa Kicks U14B IM |
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| Wed | May 21 | U9BT2 | Whitby Optimist Park | 19:00 | Whitby FC Black U9B T2 | | Cavan FC Red U9B T2 |
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| Wed | May 21 | U9B T1 | Willowdale Park | 19:00 | DeRo TFC Black U9B T1 | | Whitby FC Yellow U9B T1 |
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| Wed | May 21 | U11BT2 | Wilson Assembly Field #2 | 19:00 | Kawartha Inferno U11B T2 | | Pickering FC Grey U11B T2 |
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| Thu | May 22 | U15BIM | Centennial Turf Ajax | 21:00 | DeRo TFC U15B IM | | Peterborough City U15B IM |
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| Thu | May 22 | U9G T2 | Maple Leaf Lower North | 18:30 | Cavan FC Red U9G T2 | | Kawartha Inferno U9G T2 |
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| Thu | May 22 | U12GT2 | Pickering Soccer Centre A | 19:00 | Pickering FC White U12G T2 | | Northumberland U12G T2 |
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| Thu | May 22 | U12GT1 | Pickering Soccer Centre B | 19:00 | Pickering FC Black U12G T1 | | FC Durham U12G T1 |
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| Thu | May 22 | U16G | Zwicks #2 | 18:30 | Belleville U16G | 4 - 0 | Cavan FC U16G |
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| Thu | May 22 | U18B | Zwicks #2 | 20:30 | Belleville U18B | | Northumberland U18B |
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| Sat | May 24 | U15GIM | Downsview Park #2 | 13:30 | North Toronto U15G IM | | Pickering FC U15G IM |
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| Sat | May 24 | U16BIM | Jayde Riviere Turf Field | 20:00 | Pickering FC U16B IM | | Peterborough City U16B IM |
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| Sun | May 25 | U14BIM | Jayde Riviere Turf Field | 18:00 | Pickering FC U14B IM | | Darlington Energy U14B IM |
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| Sun | May 25 | U14BIM | Pine Ridge HS Turf | 13:00 | DeRo TFC U14B IM | | NDUFC U14B IM |
