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| Mon | May 11 | IMG13 | Concord Thornhill Turf 1 | 19:30 | GS Juve Gu13 IM | | South Simcoe Gu13 IM |
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| Mon | May 11 | IMG13 | Milliken Mills Complex A | 19:00 | Umsc Gu13 IM | | DFC Gu13 IM |
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| Mon | May 11 | IMQG15 | Milliken Mills Complex E | 19:00 | Umsc Gu15 IMQ | 1 - 0 | Vaughan Gu15 IMQ |
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| Mon | May 11 | IMQG15 | Rainbow Creek | 21:15 | Woodbridge Gu15 IMQ | 8 - 0 | RH Green Gu15 IMQ |
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| Mon | May 11 | IMQ17 | South Courtice Turf | 21:00 | Darlington Gu17 IMQ | 1 - 0 | Vaughan Gu17 IMQ |
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| Tue | May 12 | IMQG16 | Crosby Park Richmond Hill | 19:00 | RH Green Gu16 IMQ | 0 - 1 | Woodbridge Gu16 IMQ |
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| Tue | May 12 | IMQG16 | Dr GW Williams SS | 21:00 | DFC Gu16 IMQ | 2 - 1 | Newmarket Gu16 IMQ |
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| Tue | May 12 | IMQG16 | J. C. Massie Field | 21:00 | Barrie Gu16 IMQ | 0 - 4 | Umsc Gu16 IMQ |
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| Tue | May 12 | B13IM | Joe Magani Field | 19:00 | Bradford Wolves Bu13 IM | | South Simcoe Bu13 IM |
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| Tue | May 12 | B13IM | Max Stiles | 19:00 | DFC Bu13 IM | | Muskoka United Bu13 IM |
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| Tue | May 12 | B13IM | Richardson Park #7 | 19:00 | Newmarket Red Bu13 IM | | Jarvis Bu13 IM |
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| Tue | May 12 | IMQG16 | Stewart Burnett Park | 21:00 | Aurora Gu16 IMQ | 4 - 0 | GS Juve Gu16 IMQ |
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| Tue | May 12 | B13IM | Summit Park | 19:00 | Knsc Bu13 IM | | RH White Bu13 IM |
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| Tue | May 12 | B13IM | Villanova North | 19:00 | King United Bu13 IM | | KO Bu13 IM |
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| Tue | May 12 | B13IM | Wade Gate | 18:30 | Vaughan Bu13 IM | | Ssc Bu13 IM |
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| Wed | May 13 | IMQ17 | Dr. Denison Turf - Newmarket | 21:00 | Newmarket Gu17 IMQ | | PCSC Gu17 IMQ |
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| Wed | May 13 | IMQ17 | J. C. Massie Field | 21:00 | Barrie Gu17 IMQ | | THPFC Gu17 IMQ |
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| Wed | May 13 | PQAb15 | Richmond Green West | 19:00 | RH Green Bu15 IMPQA | 4 - 1 | Newmarket Bu15 IMPQB |
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| Wed | May 13 | IMQ17 | Ross Lord 5 | 18:30 | NT Gu17 IMQ | 0 - 5 | Cherry Beach Gu17 IMQ |
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| Wed | May 13 | IMQ17 | Stewart Burnett Park | 21:00 | Aurora Gu17 IMQ | | Whitby Gu17 IMQ |
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| Thu | May 14 | IMQG14 | Concord Thornhill North 1 | 19:30 | GS Juve Gu14 IMQ | | DFC Gu14 IMQ |
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| Thu | May 14 | IMQG14 | Eastview Park B | 19:00 | Barrie Gu14 IMQ | | Umsc Gu14 IMQ |
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| Thu | May 14 | IMQG14 | Frank Stronach Park | 19:00 | Newmarket Gu14 IMQ | | Vaughan Gu14 IMQ |
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| Thu | May 14 | IMQG14 | OS #1 | 18:00 | Woodbridge Gu14 IMQ | | Knsc Gu14 IMQ |
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| Fri | May 15 | IMQG14 | Stewart Burnett Park | 21:00 | Aurora Gu14 IMQ | | Bryst Gu14 IMQ |
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| Sat | May 16 | IMQG15 | Barrie Sports Complex #2 | 18:00 | Barrie Gu15 IMQ | | Newmarket Gu15 IMQ |
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| Sat | May 16 | QAB17 | Barrie Sports Complex #2 | 21:00 | Barrie Bu17 IMQA | | Bryst Bu17 IMQA |
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| Sat | May 16 | IMQG16 | Centennial Park Markham | 19:00 | Markham Black Gu16 IMQ | | Nipissing Gu16 IMQ |
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| Sat | May 16 | IMQG14 | Dr. Denison Turf - Newmarket | 11:00 | Newmarket Gu14 IMQ | | Knsc Gu14 IMQ |
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| Sat | May 16 | IMG13 | Emily Carr SS | 10:30 | Woodbridge Gu13 IM | | Newmarket Gu13 IM |
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| Sat | May 16 | IMQ17 | Holy Cross SS - Peterborough | 13:15 | PCSC Gu17 IMQ | | Barrie Gu17 IMQ |
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| Sat | May 16 | B13IM | Huntington Park Mini West | 09:30 | Thornhill Bolts Bu13 IM | | Umsc Bu13 IM |
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| Sat | May 16 | IMQ17 | Iroquois Park | 10:00 | Whitby Gu17 IMQ | | GS Juve Gu17 IMQ |
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| Sat | May 16 | IMQ17 | Keelesdale South Park | 19:00 | Etobicoke FC Gu17 IMQ | | NT Gu17 IMQ |
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| Sat | May 16 | IMQG14 | Machell Park | 18:30 | DFC Gu14 IMQ | | Barrie Gu14 IMQ |
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| Sat | May 16 | QAB17 | McNaughton Turf | 11:00 | Vaughan Bu17 IMQA | | Thornhill Bolts Bu17 IMQA |
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| Sat | May 16 | IMQG15 | McNaughton Turf | 14:00 | Vaughan Gu15 IMQ | | Woodbridge Gu15 IMQ |
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| Sat | May 16 | IMQG14 | McNaughton Turf | 16:00 | Vaughan Gu14 IMQ | | Bryst Gu14 IMQ |
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| Sat | May 16 | QBB17 | Nipissing University | 13:00 | Nipissing Bu17 IMQB | | Jarvis Bu17 IMQB |
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| Sat | May 16 | IMQG16 | Richmond Green West | 13:00 | RH Green Gu16 IMQ | | Newmarket Gu16 IMQ |
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| Sat | May 16 | IMQG15 | Richmond Green West | 15:00 | RH Green Gu15 IMQ | | Sudbury Gu15 IMQ |
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| Sat | May 16 | QBB17 | Villanova Turf | 19:00 | King United Bu17 IMQB | | Aurora Bu17 IMQB |
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| Sun | May 17 | IMQG15 | Barrie Sports Complex #2 | 18:00 | Barrie Gu15 IMQ | | Vaughan Gu15 IMQ |
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| Sun | May 17 | IMQG15 | Concord Thornhill Turf 1 | 21:00 | GS Juve Gu15 IMQ | | Newmarket Gu15 IMQ |
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| Sun | May 17 | IMQG16 | Dr. Denison Turf - Newmarket | 14:00 | Newmarket Gu16 IMQ | | Nipissing Gu16 IMQ |
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| Sun | May 17 | IMQG15 | Milliken Mills Complex E | 19:00 | Umsc Gu15 IMQ | | KO Gu15 IMQ |
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| Sun | May 17 | B13IM | Stewart Burnett Park | 09:00 | Aurora Bu13 IM | | Prime FC Bu13 IM |
