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| Mon | May 18 | U12GT2 | Portage Park | 19:00 | Whitby FC White U12G T2 | | Oshawa Kicks U12G T2 |
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| Tue | May 19 | U15B | Alexandra Park | 19:00 | Oshawa Kicks White U15B | | Peterborough White U15B |
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| Tue | May 19 | U10GT1 | Chopin Park #1 | 18:00 | FC Durham Black E U10G T1 | | Whitby FC Yellow U10G T1 |
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| Tue | May 19 | U10GT2 | Chris Graham 1 | 18:30 | Pickering FC Grey U10G T2 | | Darlington Rush U10G T2 |
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| Tue | May 19 | U16GIM | Civic Field #3 (Durham) | 21:00 | Oshawa Kicks U16GIM | | Pickering FC U16GIM |
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| Tue | May 19 | U15B | Connaught Park (Oshawa) | 19:00 | Oshawa Turul Synergy U15B | 6 - 3 | MFA U15B |
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| Tue | May 19 | U10GT1 | Darlington Field #2 | 18:45 | Darlington Energy U10G T1 | | FC Durham Black W U10G T1 |
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| Tue | May 19 | U15B | Darlington Field #3 | 19:00 | Darlington Rush U15B | 5 - 2 | Oshawa Turul Green U15B |
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| Tue | May 19 | U16GIM | Darlington Field #4 | 19:00 | Darlington Energy U16GIM | 1 - 12 | East York U16GIM |
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| Tue | May 19 | U13BT2 | Darlington Field #5 | 18:30 | Darlington Rush U13B T2 | | Cavan FC Black U13B T2 |
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| Tue | May 19 | U16B | Eastgate #1 | 21:00 | Peterborough White U16B | | Darlington Rush U16B |
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| Tue | May 19 | U16GIM | Eglinton Flats 11 | 21:00 | THPFC U16GIM | | NT Nitros U16GIM |
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| Tue | May 19 | U16BIM | Fleming Knights West Turf | 20:30 | Peterborough U16BIM | | Oshawa Kicks U16BIM |
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| Tue | May 19 | U8G | Glenbourne Park #1 5v5 | 19:00 | Oshawa Kicks Red U8G | | Pickering FC Black U8G |
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| Tue | May 19 | U8G | Glenbourne Park #2 5v5 | 19:00 | Oshawa Kicks White U8G | | Whitby FC Yellow U8G |
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| Tue | May 19 | U8G | Gordon #5 | 18:00 | Whitby FC Blue U8G | | Darlington Energy U8G |
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| Tue | May 19 | U8G | Gordon #5 | 19:00 | Whitby FC White U8G | | NDUFC U8G |
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| Tue | May 19 | U10GT1 | Guthrie Park West | 19:00 | Whitby FC Blue U10G T1 | | NDUFC U10G T1 |
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| Tue | May 19 | U16GIM | Iroquois Park | 19:00 | Whitby FC U16GIM | | Northumberland U16GIM |
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| Tue | May 19 | U16BIM | Iroquois Park | 21:00 | Whitby FC U16BIM | | Darlington Energy U16B IM |
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| Tue | May 19 | U10GT1 | James Cockburn #1 | 19:00 | Northumberland U10G T1 | | Pickering FC Black U10G T1 |
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| Tue | May 19 | U14GIM | Kinsmen Park #1 Ajax | 18:30 | FC Durham U14GIM | 6 - 3 | Belleville U14GIM |
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| Tue | May 19 | U13BT2 | Kinsmen Park 1 - Pickering | 18:30 | Pickering FC Grey U13B T2 | | Northumberland Blue U13B T2 |
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| Tue | May 19 | U16BIM | Kinsmen Park 2 | 21:00 | Pickering FC U16BIM | | DeRo TFC U16BIM |
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| Tue | May 19 | U8G | Kinsmen Park 4 - #1 | 18:30 | Pickering FC Grey U8G | | FC Durham U8G |
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| Tue | May 19 | U16GIM | LAmoreaux #1 | 21:00 | CTSA G3 Blue U16GIM | | Peterborough U16GIM |
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| Tue | May 19 | U13BT2 | Laval Park | 19:00 | Oshawa Kicks White U13B T2 | 0 - 0 | MFA U13B T2 |
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| Tue | May 19 | U16B | Lions Park 2 Cobourg | 19:00 | Northumberland U16B | | Whitby FC U16B |
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| Tue | May 19 | U10GT2 | Maple Leaf Lower South | 18:30 | Cavan FC Black U10G T2 | | Oshawa Kicks White U10G T2 |
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| Tue | May 19 | U13BT1 | McLaughlin Park | 19:00 | Oshawa Turul Thunderbirds U13B T1 | | Peterborough Blue U13B T1 |
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| Tue | May 19 | U13BT1 | Miles Park | 19:00 | Dero TFC Black U13B T1 | | Oshawa Turul United U13B T1 |
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| Tue | May 19 | U10GT2 | Optimist Park 4 Kawartha Lakes | 19:00 | Kawartha Inferno U10G T2 | | Cavan FC Red U10G T2 |
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| Tue | May 19 | U10GT1 | Parkwood Meadows Park | 19:00 | Oshawa Kicks Red U10G T1 | | FC Durham Blue W U10G T1 |
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| Tue | May 19 | U16G | Peel Park | 21:00 | Whitby FC U15G | | Oshawa Turul U16G |
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| Tue | May 19 | U13BT1 | Terry Fox Park | 19:00 | Oshawa Kicks Red U13B T1 | 0 - 0 | FC Durham Blue W U13B T1 |
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| Tue | May 19 | U13BT2 | Uxbridge Field #18 | 19:00 | NDUFC U13B T2 | 0 - 0 | Northumberland Black U13B T2 |
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| Tue | May 19 | U10GT2 | Whitby Optimist Park | 19:00 | Whitby FC White U10G T2 | | Peterborough U10G T2 |
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| Wed | May 20 | U11BT1 | Airmens Park | 19:00 | Oshawa Turul Predators U11B T1 | | FC Durham Blue E U11B T1 |
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| Wed | May 20 | U14BT1 | Ajax HS - 11v11 | 18:30 | FC Durham U14B T1 | | Darlington Rush U14B T1 |
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| Wed | May 20 | U14BT2 | Baulch Road 2 | 19:00 | Northumberland U14B T2 | | Pickering FC White U14B T2 |
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| Wed | May 20 | U11BT2 | Beavermead #5 | 19:00 | Peterborough White U11B T2 | | Pickering FC Grey U11B T2 |
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| Wed | May 20 | U9BT2 | Brookside Park | 19:00 | Oshawa Turul U9B | | Pickering FC White U9B |
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| Wed | May 20 | U12BT2 | CCC 2 | 19:00 | Northumberland U12B T2 | | Oshawa Turul Azzuri U12B T2 |
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| Wed | May 20 | U12BT1 | Chopin Park #1 | 18:30 | FC Durham Black E U12B T1 | | FC Durham Black W U12B T1 |
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| Wed | May 20 | U12BT1 | Chopin Park #2 | 18:30 | FC Durham Blue E U12B T1 | | Northumberland U12B T1 |
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| Wed | May 20 | U11BT2 | Chris Graham 2 | 18:30 | Pickering FC White U11B T2 | | Oshawa Kicks White U11B T2 |
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| Wed | May 20 | U11BT1 | Chris Graham 3 | 18:30 | Pickering FC Black U11B T1 | | FC Durham Black E U11B T1 |
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| Wed | May 20 | U9BT2 | Darlington Field #1 | 18:00 | Darlington Dash U9B | | FC Durham White W U9B |
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| Wed | May 20 | U9B T1 | Darlington Field #1 | 19:00 | Darlington Energy U9B | | FC Durham Black W U9B |
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| Wed | May 20 | U11BT1 | Darlington Field #2 | 18:00 | Darlington Energy U11B T1 | | DeRo TFC Black U11B T1 |
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| Wed | May 20 | U11BT2 | Darlington Field #2 | 19:10 | Darlington Power U11B T2 | | Northumberland Black U11B T2 |
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| Wed | May 20 | U12BT1 | Darlington Field #5 | 18:00 | Darlington Energy U12B T1 | | DeRo TFC Red U12B T1 |
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| Wed | May 20 | U12BT2 | Darlington Field #5 | 19:15 | Darlington Rush U12B T2 | | Kawartha Inferno U12B T2 |
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| Wed | May 20 | U18G | Dr GW Williams SS | 21:15 | Aurora FC U18G | | THPFC U18G |
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| Wed | May 20 | U14BT2 | Eastgate #2 | 19:00 | Peterborough U14B T2 | | Kawartha Inferno U14B T2 |
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| Wed | May 20 | U12BT2 | Eastgate #3 | 19:00 | Peterborough Blue U12B T2 | | NDUFC U12B T2 |
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| Wed | May 20 | U9B T1 | Fishlock #3 | 18:00 | FC Durham Blue W U9B | | DeRo TFC Red U9B |
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| Wed | May 20 | U18G | Fleming PYSC East Turf | 21:00 | Peterborough U18G | | MFA U17G |
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| Wed | May 20 | U9B T1 | Gordon #5 | 18:00 | Whitby FC Blue U9B | | Oshawa Kicks Red U9B |
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| Wed | May 20 | U9BT2 | Gordon #5 | 19:00 | Whitby FC White U9B | | Oshawa Kicks White U9B |
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| Wed | May 20 | U14BIM | Iroquois Park | 19:00 | Whitby FC U14BIM | | Darlington Energy U14BIM |
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| Wed | May 20 | U11BT2 | James Cockburn #1 | 19:00 | Northumberland Blue U11B T2 | | FC Durham White W U11B T2 |
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| Wed | May 20 | U11BT2 | James Cockburn #2 | 19:00 | Northumberland Red U11B T2 | | Darlington Dash U11B T2 |
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| Wed | May 20 | U12BT1 | Kinsmen Park 1 - Pickering | 18:30 | Pickering FC Grey U12B T1 | | Whitby FC Blue U12B T1 |
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| Wed | May 20 | U9BT2 | Kinsmen Park 4 - #1 | 18:30 | Pickering FC Green U9B | | Whitby FC Red U9B |
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| Wed | May 20 | U9B T1 | Kinsmen Park 4 - #2 | 18:30 | Pickering FC Grey U9B | | Pickering FC Black U9B |
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| Wed | May 20 | U18G | Lions Park 2 Cobourg | 19:00 | Northumberland U18G | | Cavan FC U18G |
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| Wed | May 20 | U12BT2 | Maple Leaf Lower | 19:45 | Cavan FC U12B T2 | | Dero TFC Black U12B T2 |
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| Wed | May 20 | U11BT2 | Maple Leaf Lower North | 18:30 | Cavan FC Black U11B T2 | | MFA U11B T2 |
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| Wed | May 20 | U11BT1 | Maple Leaf Lower South | 18:30 | Cavan FC Red U11B T1 | | Whitby FC Yellow U11B T1 |
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| Wed | May 20 | U14BT1 | Maple Leaf Upper | 20:00 | Cavan FC U14B T1 | | Northumberland U14B T1 |
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| Wed | May 20 | U11BT1 | Maple Leaf Upper South | 18:30 | Cavan FC White U11BT1 | | Whitby FC Blue U11B T1 |
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| Wed | May 20 | U12BT1 | McLaughlin Park | 19:00 | Oshawa Turul Titans U12B T1 | | Pickering FC Black U12B T1 |
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| Wed | May 20 | U18G | North Oshawa Park | 21:00 | Oshawa Kicks U18G | | Darlington Energy U18G |
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| Wed | May 20 | U12BT2 | Nottingham Field 9v9 1 | 18:30 | FC Durham Blue W U12B T2 | | FC Durham White W U2B T2 |
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| Wed | May 20 | U11BT1 | Parkwood Meadows Park | 19:00 | Oshawa Kicks Red U11B T1 | | Oshawa Turul Flames U11B T1 |
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| Wed | May 20 | U14BT1 | Peel Park | 19:00 | Whitby FC White U14B T1 | | Oshawa Kicks White U14B T1 |
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| Wed | May 20 | U15B | Peel Park | 21:00 | Whitby FC U15B | | NDUFC U15B |
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| Wed | May 20 | U11BT1 | Pine Ridge #1 | 18:30 | FC Durham Black W U11B T1 | | Peterborough Blue U11B T1 |
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| Wed | May 20 | U11BT1 | Pine Ridge #2 | 18:30 | FC Durham Blue W U11B T1 | | DeRo TFC Red U11B T1 |
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| Wed | May 20 | U12BT1 | Portage Park | 19:00 | Whitby FC Yellow U12B T1 | | Oshawa Kicks Red U12B T1 |
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| Wed | May 20 | U14BIM | Quinte West - Centennial #1 | 19:00 | QW Wolverines U14BIM | | Oshawa Turul U14BIM |
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| Wed | May 20 | U9B T1 | St. Catherines of Siena School | 19:00 | DeRo TFC Black U9B | | FC Durham Black E U9B |
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| Wed | May 20 | U12BT2 | Terry Fox Park | 19:00 | Oshawa Kicks White U12B T2 | | Peterborough White U12B T2 |
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| Wed | May 20 | U11BT2 | Uxbridge Field #14 | 19:00 | NDUFC U11B T2 | | Darlington Rush U11B T2 |
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| Wed | May 20 | U9BT2 | Uxbridge Field #8 | 19:00 | NDUFC U9B | | Darlington Rush U9B |
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| Thu | May 21 | U11GT2 | Airmens Park | 19:00 | Oshawa Turul U11G T2 | | Peterborough Blue U11G T2 |
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| Thu | May 21 | U17B | Centennial Turf Ajax | 19:00 | MFA U17BIM | | Pickering FC U17BIM |
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| Thu | May 21 | U11GT1 | Chopin Park #1 | 18:00 | FC Durham Black E U11G T1 | | Darlington Energy U11GT1 |
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| Thu | May 21 | U12GT1 | Chopin Park #1 | 19:00 | FC Durham Black E U12G T1 | | FC Durham Black W U12G T1 |
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| Thu | May 21 | U12GT1 | Chopin Park #2 | 18:00 | FC Durham Blue E U12G T1 | | Darlington Energy U12G T1 |
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| Thu | May 21 | U11GT2 | Chris Graham 1 | 18:30 | Pickering FC Black U11G T2 | | Northumberland Black U11G T2 |
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| Thu | May 21 | U17B | Civic Field #3 (Durham) | 21:00 | Oshawa Kicks U17BIM | | DeRo TFC U17BIM |
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| Thu | May 21 | U11GT2 | Darlington Field #2 | 19:00 | Darlington Rush U11G T2 | | Cavan FC U11G T2 |
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| Thu | May 21 | U14GIM | Darlington Field #4 | 19:00 | Darlington Energy U14GIM | | Peterborough U14GIM |
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| Thu | May 21 | U12GT2 | Eastgate #3 | 19:00 | Peterborough Blue U12G T2 | | Pickering FC Grey U12G T2 |
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| Thu | May 21 | U9G T1 | Fishlock #1 | 18:00 | FC Durham Black E U9G | | Oshawa Kicks Red U9G |
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| Thu | May 21 | U9G T1 | Fishlock #2 | 18:00 | FC Durham Black W U9G | | Darlington Energy U9G |
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| Thu | May 21 | U15BIM | Fleming Knights West Turf | 20:30 | Peterborough U15BIM | | Oshawa Kicks Red U15BIM |
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| Thu | May 21 | U9G T1 | Gordon #5 | 18:00 | Whitby FC Yellow U9G | | Pickering FC Black U9G |
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| Thu | May 21 | U9G T2 | Gordon #5 | 19:00 | Whitby FC White U9G | | NDUFC U9G |
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| Thu | May 21 | U15BIM | Holy Cross SS - Peterborough | 21:00 | Cavan FC U15BIM | | FC Durham U15BIM |
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| Thu | May 21 | U15BIM | Iroquois Park | 19:00 | Whitby FC U15BIM | | Darlington Energy U15BIM |
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| Thu | May 21 | U17B | Iroquois Park | 21:00 | Whitby FC U17BIM | | Oshawa Turul U17BIM |
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| Thu | May 21 | U11GT2 | James Cockburn #1 | 19:00 | Northumberland Blue U11G T2 | | Peterborough White U11G T2 |
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| Thu | May 21 | U9G T2 | Kinsmen Park 4 - #1 | 18:30 | Pickering Grey FC U9G | | Darlington Rush U9G |
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| Thu | May 21 | U11GT1 | Lakeside (Ajax) #1 | 18:30 | FC Durham Black W U11G T1 | | Oshawa Kicks White U11G T1 |
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| Thu | May 21 | U16G | Lions Park 1 Cobourg | 19:00 | Northumberland U15G | | Darlington Rush U15G |
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| Thu | May 21 | U16G | Maple Leaf Lower | 19:00 | Cavan FC U15G | | Oshawa Kicks U15G |
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| Thu | May 21 | U12GT2 | Maple Leaf Upper | 19:00 | Cavan FC Black U12G T2 | | Northumberland U12G T2 |
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| Thu | May 21 | U15BIM | Monarch Turf (Ajax) | 21:00 | DeRo TFC U15BIM | | NDUFC U15BIM |
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| Thu | May 21 | U11GT1 | Parkwood Meadows Park | 19:00 | Oshawa Kicks Red U11G T1 | | Whitby FC Blue U11G T1 |
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| Thu | May 21 | U14GIM | Peel Park | 21:00 | Whitby FC U14GIM | | FC Durham U14GIM |
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| Thu | May 21 | U12GT1 | Portage Park | 19:00 | Whitby FC Yellow U12G T1 | | Cavan FC Red U12G T1 |
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| Thu | May 21 | U11GT2 | Scugog Field #5 | 19:00 | NDUFC U11G T2 | | Whitby FC White U11G T2 |
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| Thu | May 21 | U12GT2 | Wilson Assembly Field #2 | 19:00 | Kawartha Inferno U12G T2 | | Darlington Rush U12G T2 |
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| Thu | May 21 | U16G | Wilson Field Upper #3 | 19:00 | Kawartha U16G | | Peterborough U15G |
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| Sat | May 23 | U16GIM | Iroquois Park | 12:00 | Whitby FC U16GIM | | THPFC U16GIM |
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| Sat | May 23 | U14GIM | Kinsmen Park 3 | 11:00 | Pickering FC U14GIM | | Belleville U14GIM |
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| Sat | May 23 | U16BIM | Vaso Field | 16:00 | Oshawa Turul U16BIM | | FC Durham U16BIM |
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| Sun | May 24 | U15BIM | Beverley Morgan Park | 12:00 | Pickering FC U15BIM | | DeRo TFC U15BIM |
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| Sun | May 24 | U14BIM | Beverley Morgan Park | 14:00 | DeRo TFC U14BIM | | Oshawa Kicks Red U14BIM |
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| Sun | May 24 | U16BIM | Beverley Morgan Park | 16:00 | DeRo TFC U16BIM | | QW Wolverines U16BIM |
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| Sun | May 24 | U16GIM | Civic Field #3 (Durham) | 12:00 | Oshawa Kicks U16GIM | | NT Nitros U16GIM |
