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| Mon | Sep 14 | U14BT1 | Baulch Road 1 | 18:30 | Northumberland U14B T1 | 3 - 1 | FC Durham U14B T1 |
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| Mon | Sep 14 | U9B T1 | Darlington Field #2 | 18:00 | Darlington Energy U9B | | Pickering FC Grey U9B |
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| Mon | Sep 14 | U13BT2 | Eastgate #3 | 18:00 | Peterborough White U13B T2 | 0 - 0 | Kawartha Inferno Black U13B T2 |
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| Mon | Sep 14 | U9B T1 | Fishlock #2 | 18:00 | FC Durham Blue W U9B | | Pickering FC Black U9B |
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| Mon | Sep 14 | U9G T2 | Glenbourne Park #1 5v5 | 19:00 | Oshawa Kicks White U9G | | Darlington Rush U9G |
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| Mon | Sep 14 | U9B T1 | Glenbourne Park #2 5v5 | 18:00 | Oshawa Kicks Red U9B | | DeRo TFC Red U9B |
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| Mon | Sep 14 | U13BT2 | Imaje Sports Field | 18:30 | MFA U13B T2 | 0 - 0 | Cavan FC Black U13B T2 |
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| Mon | Sep 14 | U14BT2 | Kinsmen Park 2 | 19:30 | Pickering FC White U14B T2 | 0 - 5 | Oshawa Turul U14B T2 |
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| Mon | Sep 14 | U9G T2 | Kinsmen Park 4 - #2 | 18:30 | Pickering Grey FC U9G | | NDUFC U9G |
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| Mon | Sep 14 | U14BT2 | Lions Park 1 Cobourg | 18:30 | Northumberland U14B T2 | 0 - 8 | Peterborough U14B T2 |
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| Mon | Sep 14 | U14G | Maple Leaf Upper | 19:00 | Cavan FC U14G | 0 - 1 | Northumberland U14G |
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| Mon | Sep 14 | U14BT1 | North Oshawa Park | 21:00 | Oshawa Kicks White U14B T1 | 1 - 0 | Pickering FC Grey U14B T1 |
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| Mon | Sep 14 | U9B T1 | Peter LeBel Central - North | 18:30 | Whitby FC Blue U9B | | FC Durham Black E U9B |
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| Mon | Sep 14 | U9G T1 | Peter LeBel Central - South | 18:30 | Whitby FC Yellow U9G | | Darlington Energy U9G |
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| Mon | Sep 14 | U12GT1 | Pine Ridge #1 | 18:00 | FC Durham Black W U12G T1 | | Whitby FC Yellow U12G T1 |
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| Mon | Sep 14 | U14BT1 | South Courtice Arena | 19:00 | Darlington Rush U14B T1 | 0 - 1 | Cavan FC U14B T1 |
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| Mon | Sep 14 | U15BIM | Uxbridge Field #15 | 19:00 | NDUFC U15BIM | 1 - 2 | Oshawa Kicks Red U15BIM |
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| Mon | Sep 14 | U11GT1 | Whitby Optimist Park | 18:30 | Whitby FC Yellow U11G T1 | | FC Durham Black W U11G T1 |
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| Mon | Sep 14 | U14G | Wilson Field Lower #1 | 18:30 | Kawartha Inferno U14G | 1 - 2 | Peterborough U14G |
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| Tue | Sep 15 | U15B | Civic Field #3 (Durham) | 21:00 | Oshawa Turul Synergy U15B | | Whitby FC U15B |
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| Tue | Sep 15 | U11GT1 | Darlington Field #2 | 18:00 | Darlington Energy U11GT1 | | Whitby FC Blue U11G T1 |
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| Tue | Sep 15 | U15B | Imaje Sports Field | 18:00 | MFA U15B | 0 - 4 | Oshawa Turul Green U15B |
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| Tue | Sep 15 | U16B | Iroquois Park Whitby | 21:00 | Whitby FC U16B | 0 - 12 | Darlington Rush U16B |
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| Tue | Sep 15 | U16BIM | Kinsmen Park 2 | 19:30 | Pickering FC U16BIM | 0 - 4 | Oshawa Turul U16BIM |
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| Tue | Sep 15 | U15B | Lions Park 1 Cobourg | 18:00 | Northumberland U15B | 5 - 1 | Peterborough White U15B |
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| Tue | Sep 15 | U11GT2 | Maple Leaf Upper North | 19:00 | Cavan FC U11G T2 | | Pickering FC Black U11G T2 |
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| Tue | Sep 15 | U13BT1 | Miles Park | 18:30 | Dero TFC Black U13B T1 | 0 - 0 | Whitby FC White U13B T1 |
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| Tue | Sep 15 | U16BIM | Monarch Park North Grass (Ajax) | 20:30 | FC Durham U16BIM | | QW Wolverines U16BIM |
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| Tue | Sep 15 | U16BIM | Monarch Turf (Ajax) | 21:00 | DeRo TFC U16BIM | | Oshawa Kicks U16BIM |
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| Tue | Sep 15 | U15B | North Oshawa Park | 18:30 | Oshawa Kicks White U15B | 0 - 4 | Darlington Rush U15B |
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| Tue | Sep 15 | U10GT2 | Optimist Park 4 Kawartha Lakes | 18:30 | Kawartha Inferno U10G T2 | | Darlington Rush U10G T2 |
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| Tue | Sep 15 | U9G T1 | Peter LeBel Central - North | 18:00 | Whitby FC Blue U9G | | FC Durham Black E U9G |
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| Tue | Sep 15 | U9B T1 | Peter LeBel Central - South | 18:30 | Whitby FC Yellow U9B | | DeRo TFC Black U9B |
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| Tue | Sep 15 | U12GT1 | Pine Ridge #1 | 18:00 | FC Durham Black E U12G T1 | | Pickering FC Black U12G T1 |
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| Tue | Sep 15 | U16BIM | Thomas A. Stewart HS | 20:30 | Peterborough U16BIM | 2 - 1 | Whitby FC U16BIM |
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| Wed | Sep 16 | U14BT1 | Alexandra Park | 18:00 | Oshawa Kicks White U14B T1 | 2 - 0 | Darlington Rush U14B T1 |
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| Wed | Sep 16 | U14BIM | Civic Field #3 (Durham) | 19:00 | Oshawa Kicks Red U14BIM | 2 - 4 | Pickering FC U14BIM |
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| Wed | Sep 16 | U14BIM | Civic Field #3 (Durham) | 21:00 | Oshawa Turul U14BIM | 2 - 4 | QW Wolverines U14BIM |
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| Wed | Sep 16 | U14BIM | Iroquois Park Whitby | 19:00 | Whitby FC U14BIM | 0 - 3 | Darlington Energy U14BIM |
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| Wed | Sep 16 | U14BT1 | Peel Park | 19:00 | Whitby FC White U14B T1 | 8 - 2 | FC Durham U14B T1 |
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| Thu | Sep 17 | U15BIM | Eastgate #1 | 20:30 | Peterborough U15BIM | 10 - 3 | NDUFC U15BIM |
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| Thu | Sep 17 | U15BIM | Fleming PYSC East Turf | 21:00 | Cavan FC U15BIM | 3 - 1 | FC Durham U15BIM |
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| Thu | Sep 17 | U15BIM | Jayde Riviere Turf Field | 19:30 | Pickering FC U15BIM | 1 - 4 | Darlington Energy U15BIM |
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| Sat | Sep 19 | U16BIM | Civic Field #3 (Durham) | 16:00 | Oshawa Kicks U16BIM | | QW Wolverines U16BIM |
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| Sat | Sep 19 | U15BIM | Fleming PYSC East Turf | 10:00 | Cavan FC U15BIM | | NDUFC U15BIM |
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| Sat | Sep 19 | U16BIM | Fleming PYSC East Turf | 13:00 | Peterborough U16BIM | | Pickering FC U16BIM |
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| Sat | Sep 19 | U15BIM | Jayde Riviere Turf Field | 19:00 | Pickering FC U15BIM | | Oshawa Kicks Red U15BIM |
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| Sat | Sep 19 | U16BIM | Monarch Park North Grass (Ajax) | 09:00 | FC Durham U16BIM | | Oshawa Turul U16BIM |
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| Sat | Sep 19 | U15BIM | Monarch Park North Grass (Ajax) | 11:00 | FC Durham U15BIM | | Peterborough U15BIM |
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| Sun | Sep 20 | U16BIM | Beverley Morgan Park | 16:00 | DeRo TFC U16BIM | | Whitby FC U16BIM |
