|
| Mon | May 25 | M21RSW | Alumni Field, Laurier | 21:00 | Waterloo United U21M | 2 - 0 | Woodstock FC U21M |
|
| Mon | May 25 | W21RCE | Consumers Field South | 21:00 | Whitby FC U21W | 0 - 5 | Pickering FC U21W |
|
| Mon | May 25 | W21RCE | Dieppe Park | 21:00 | East York U21W | 0 - 1 | NYFC Strikers U21W |
|
| Mon | May 25 | M21RC | Dufferin District 1 | 21:00 | IFC U21M | 1 - 6 | Vaughan Azzurri U21M |
|
| Mon | May 25 | M21RS | Earlscourt North | 21:00 | SC Toronto Eagles U21M | 1 - 0 | SSE 90 U21M |
|
| Mon | May 25 | MOpCup | Esther Shiner Stadium | 21:00 | North York Hearts | 2 - 1 | QPR Reg |
|
| Mon | May 25 | MOpCup | LAmoreaux #1 | 21:00 | GS United Men | 2 - 1 | East York Men |
|
| Mon | May 25 | W21RS | Norton Community Park F2 | 21:00 | Burlington SC Blue U21W | 1 - 0 | Force Academy U21W |
|
| Mon | May 25 | WOpCup | Sonoma Turf | 21:00 | KNSC Lions Women | 0 - 2 | Kitchener TFC Red |
|
| Tue | May 26 | WRS | Barbour Field 1 | 21:00 | HEADS United Hurricanes | 0 - 2 | Gryphons FC Women |
|
| Tue | May 26 | MElite | Earlscourt North | 21:10 | Peniche CC | 1 - 1 | Hrvat St. Catharines |
|
| Tue | May 26 | M21RCE | Major Abbas Ali Park East | 21:00 | Olympic Flame K19 | 2 - 0 | Whitby FC U21M |
|
| Tue | May 26 | W21RC | McNaughton Turf | 21:00 | Vaughan Azzurri U21W | 5 - 0 | Barrie Spirit U21W |
|
| Tue | May 26 | M21RS | Trafalgar Sports Park 9 | 21:00 | Georgetown Mustangs U21M | 3 - 0 | Atletico Sporting Toronto U21M |
|
| Tue | May 26 | WRS | Waterdown District HS | 21:00 | Flamborough Dundas | 0 - 6 | SSC Women |
|
| Tue | May 26 | WOpCup | Zanchin Automotive Soccer Centre Stadium | 21:00 | CFC Atletico Women | 1 - 3 | Caledon United FC W Prov |
|
| Wed | May 27 | MOpCup | Bethesda #1 | 21:30 | Stouffville Mustangs Yellow | 2 - 0 | Prostars FC |
|
| Wed | May 27 | WRCE | Centennial College | 21:00 | Pickering FC Women | 1 - 1 | West Rouge Storm Black |
|
| Wed | May 27 | WOpCup | Cherry Beach West | 21:00 | SC Toronto Eagles Women | 1 - 0 | HEADS United Hurricanes |
|
| Wed | May 27 | M21PC | Crescent School | 20:15 | Power FC U21M | | Olympiacos Toronto K21 |
|
| Wed | May 27 | WOpCup | Dr. Denison Turf - Newmarket | 21:00 | Newmarket United II W | 1 - 2 | Oshawa Kicks White |
|
| Wed | May 27 | MOpCup | Earlscourt North | 21:00 | Toronto Irish FC II | | Ebony Jrs |
|
| Wed | May 27 | WOpCup | Eastview Full 4 | 21:00 | Gryphons FC Women | | King City Royals Women |
|
| Wed | May 27 | WOpCup | Fleming PYSC East Turf | 21:00 | Peterborough City Women | | Newmarket United W Prov |
|
| Wed | May 27 | M21PS | Iceland 1 | 21:00 | Dixie U21M | | Whitecaps London U21M |
|
| Wed | May 27 | WRCE | LAmoreaux #1 | 21:00 | GS United W Reg | 0 - 4 | Oshawa Kicks Red |
|
| Wed | May 27 | M21RC | Villanova Turf | 21:00 | King City Royals U21M | | Oak Ridges Knights U21M RC |
|
| Wed | May 27 | MOpCup | Zanchin Automotive Soccer Centre Stadium | 19:00 | Atletico Toronto | | Panathinaikos |
|
| Wed | May 27 | MOpCup | Zanchin Automotive Soccer Centre Stadium | 21:00 | Stouffville Mustangs Blue | 1 - 3 | Toronto Irish FC |
|
| Thu | May 28 | WRC | Angus Glen Community Centre | 21:00 | Markham Lightning Women | | NYC Panthers |
|
| Thu | May 28 | MOpCup | Barrie SC Development Centre | 21:00 | Barrie Blazers Men RC | | Artemisium FC |
|
| Thu | May 28 | M21RC | Berczy Park Centre | 19:00 | UMSC U21M | | Barrie Spirit U21M |
|
| Thu | May 28 | M21RS | Downsview Turf 3 | 21:00 | NT Nitros U21M | | SC Toronto Eagles U21M |
|
| Thu | May 28 | WOpCup | Fountain St Soccer Complex #4 (Grass) | 21:00 | Cambridge United Women | | Caledon United FC W Reg |
|
| Thu | May 28 | M21RSW | Heritage Green #2 | 21:00 | Hamilton Croatia U21M | | Cambridge United U21M |
|
| Thu | May 28 | WProv | LAmoreaux #1 | 21:10 | GS United W Prov | | Caledon United FC W Prov |
|
| Thu | May 28 | WRS | Marden Park 1 | 21:00 | Rockwood FC Black | | Flamborough Dundas |
|
| Thu | May 28 | MOpCup | Orchard Park SS | 20:00 | Hamilton Serbians | | CTSA Tamileelam |
|
| Thu | May 28 | M21PS | Rob Ford Stadium | 21:00 | USC Karpaty U21M | | Toronto United FC U21M |
|
| Thu | May 28 | WProv | Thames Centre ORC #2 | 20:30 | Alliance FC Mustangs Women | | Vaughan Azzurri Women |
|
| Thu | May 28 | MOpCup | Trafalgar Sports Park 9 | 21:00 | Georgetown Mustangs Men | | Guelph Royals RS |
|
| Thu | May 28 | M21PC | Vaughan Grove 2 | 21:15 | Woodbridge Strikers U21M | | Jarvis SC U21M |
|
| Thu | May 28 | WProv | Villanova Turf | 21:00 | King City Royals Women | | Kitchener TFC Red |
|
| Fri | May 29 | MJE | Barrie SC Development Centre | 21:00 | Barrie Blazers Men MJ | | CFC Atletico Blue |
|
| Fri | May 29 | MElite | Centennial College | 20:30 | Toronto Celtic | | Guelph Royals Elite |
|
| Fri | May 29 | MOpCup | City View Park Centre F2 | 21:00 | Burlington Bayhawks | | KNSC Lions Men |
|
| Fri | May 29 | W21RC | Dr GW Williams SS | 21:00 | DFC Union U21W | | NT Nitros U21W |
|
| Fri | May 29 | M21RCE | Fleming Knights West Turf | 21:00 | Cavan FC U21M | | GS United U21M |
|
| Fri | May 29 | MOpCup | Humberview SS | 20:00 | Caledon United FC Men | | Mississauga Croatia Men |
|
| Fri | May 29 | W21RS | Kiwanis Park - Niagara | 21:00 | Roma Wolves U21W | | Burlington SC Blue U21W |
|
| Fri | May 29 | MElite | LAmoreaux #1 | 21:00 | Scarboro Azzurri Blues Elite | | GS United Men |
|
| Fri | May 29 | MOpCup | Mount Joy Turf | 21:00 | Markham Lightning Men | | Toronto Pamir |
|
| Fri | May 29 | MElite | Paramount Fine Foods Centre 1 | 21:00 | Olimpia Elite | | Croatia Norval Men |
|
| Fri | May 29 | MOpCup | Paul Coffey Park | 21:00 | Distinctionz Men MJ | | Hrvat St. Catharines |
|
| Fri | May 29 | W21RS | Sherwood Park #1 Saltfleet | 20:00 | SSC U21W | | RED Academy U21W |
|
| Fri | May 29 | MOpCup | Vaughan Grove 1 | 21:15 | Woodbridge Strikers Men | | Olympiakos SC |
|
| Sat | May 30 | MOpCup | Ajax Turf Field | 18:45 | PFC Galacticos | | Cavan FC Men |
|
| Sat | May 30 | MOpCup | Centennial College | 21:00 | Scarborough Town FC RCE | | Distinctionz Men PW |
|
| Sat | May 30 | MOpCup | Keelesdale | 21:00 | CFC Atletico Black | | Sporting Club Ideal De Brampton |
|
| Sat | May 30 | MOpCup | McNicoll Park | 19:00 | SPG Red Devils United | | Peterborough City Men |
|
| Sat | May 30 | WRCE | Monarch Park North Grass (Ajax) | 16:30 | PFC Valkyries | | Cavan FC Women |
|
| Sun | May 31 | WRSW | Banat Park | 17:00 | Banat FC | | Woodstock FC Women |
|
| Sun | May 31 | W21RC | Barrie SC Development Centre | 17:00 | Barrie Spirit U21W | | Bolton Wanderers U21W |
|
| Sun | May 31 | M21RC | Barrie SC Development Centre | 21:00 | Barrie Spirit U21M | | IFC U21M |
|
| Sun | May 31 | WRC | Brickyard | 18:00 | Olimpia Toronto Women | | Nottawasaga FC |
|
| Sun | May 31 | WRC | Dr. Denison Turf - Newmarket | 19:00 | Newmarket United II W | | UMSC Women |
|
| Sun | May 31 | WRCE | Fleming PYSC East Turf | 21:00 | Peterborough City Women | | GS United W Reg |
|
| Sun | May 31 | WRC | Keelesdale | 21:00 | CFC Atletico Women | | Mississauga Croatia Women |
|
| Sun | May 31 | MElite | LAmoreaux #1 | 19:00 | Panathinaikos | | Vaughan Azzurri Elite |
|
| Sun | May 31 | MOpCup | LAmoreaux #1 | 21:00 | Scarboro Azzurri Blues Elite | | Olimpia Toronto II |
|
| Sun | May 31 | MRCE | LAmoreaux #5 | 19:00 | Scarborough Rangers | | East York Men |
|
| Sun | May 31 | MOpCup | Meadowvale (Syntex) | 20:45 | AC Diavoli | | Pana 2.0 |
|
| Sun | May 31 | M21PS | N. London Stadium | 16:00 | Whitecaps London U21M | | Toronto United FC U21M |
|
| Sun | May 31 | W21RC | Orangeville Lions Sports Park Full | 19:00 | Storm FC U21W | | Etobicoke FC U21W |
|
| Sun | May 31 | M21PS | St. Francis Xavier Catholic SS Milton | 20:30 | Scrosoppi FC U21M | | Croatia Norval U21M |
|
| Sun | May 31 | MOpCup | St. Maximillion Kolbe HS | 16:00 | DFC Union Men | | Croatia Norval Men |
|
| Sun | May 31 | W21RCE | Uxbridge Field #15 | 20:00 | NDUFC U21W | | NYFC Strikers U21W |
