| Game # | Date | Time | Team | Opponent | Venue | Score | Result |
| Sep 29 2019 | 2:30 PM | Atom LL | Woodstock Wildcats | Woolwich Twp (St. Jacobs) | 4-0 | W |
| PWLL40 | Oct 05 2019 | 4:00 PM | Peewee LL | Guelph Jr. Gryphons Red | Exhibition | 1-1 | T |
| PWLL14 | Oct 13 2019 | 11:15 AM | Peewee LL | Cambridge Roadrunners 1 | Sports Park (South) | | |
| Oct 19 2019 | 9:20 AM | Novice LL #1 | Wilmot Wolverines | Woolwich Mem (Snyder) | | |
| PWLL88 | Oct 19 2019 | 11:20 AM | Peewee LL | Waterloo Ravens #1 | Woolwich Mem (Snyder) | | |
| MILL20 | Oct 19 2019 | 3:15 PM | Intermediate | Kitchener Lady Rangers Red | Activa (Alumni) | | |
| ALL86 | Oct 19 2019 | 6:30 PM | Atom LL | Guelph Jr. Gryphons White | Woolwich Twp (St. Jacobs) | | |
| MLL112 | Oct 20 2019 | 5:30 PM | Midget LL | Guelph Jr Gryphons Black | Woolwich Twp (St. Jacobs) | | |
| MILL24 | Oct 20 2019 | 8:45 PM | Intermediate | Kitchener Lady Rangers Red | Grand River | | |
| ALL87 | Oct 26 2019 | 12:20 PM | Atom LL | Waterloo Ravens #2 | Woolwich Mem (Snyder) | | |
| Oct 26 2019 | 12:30 PM | Novice LL #1 | Wilmot Wolverines | Wilmot Rec Complex | | |
| MLL111 | Oct 26 2019 | 6:30 PM | Midget LL | Guelph Jr. Gryphons Red | Woolwich Twp (St. Jacobs) | | |
| Oct 27 2019 | 12:15 PM | Novice LL #2 | Cambridge Roadrunners | Cambridge Sports Park | | |
| BLL47 | Oct 27 2019 | 6:30 PM | Bantam LL | Grand River Mustangs | Woolwich Twp (St. Jacobs) | | |
| MILL15 | Oct 27 2019 | 8:00 PM | Intermediate | Guelph Jr. Gryphons Blue | Centennial (Guelph) | | |
| Nov 02 2019 | 9:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |
| PWLL86 | Nov 02 2019 | 4:30 PM | Peewee LL | Cambridge Roadrunners 2 | Woolwich Twp (St. Jacobs) | | |
| MLL026 | Nov 02 2019 | 6:30 PM | Midget LL | Grand River Mustangs 1 | Fergus (B) | | |
| MILL28 | Nov 02 2019 | 6:30 PM | Intermediate | Cambridge Roadrunners | Woolwich Twp (St. Jacobs) | | |
| ALL68 | Nov 03 2019 | 1:00 PM | Atom LL | Waterloo Ravens #3 | Moses Springer | | |
| MLL096 | Nov 03 2019 | 9:00 PM | Midget LL | Waterloo Ravens #4 | RIM Park (Pillers) | | |
| MILL25 | Nov 07 2019 | 7:30 PM | Intermediate | Kitchener Lady Rangers Red | Woolwich Mem (Snyder) | | |
| Nov 09 2019 | 10:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| ALL88 | Nov 09 2019 | 4:30 PM | Atom LL | Wilmot Wolverines #2 | Woolwich Twp (St. Jacobs) | | |
| ALL04 | Nov 10 2019 | 11:15 AM | Atom LL | Cambridge Roadrunners | Sports Park (South) | | |
| PWLL70 | Nov 10 2019 | 2:00 PM | Peewee LL | Waterloo Ravens #2 | Moses Springer | | |
| MILL26 | Nov 10 2019 | 5:30 PM | Intermediate | Grand River Mustangs | Woolwich Twp (St. Jacobs) | | |
| MLL114 | Nov 14 2019 | 7:30 PM | Midget LL | Cambridge Roadrunners | Woolwich Mem (Snyder) | | |
| Nov 16 2019 | 9:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| Nov 16 2019 | 10:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |
| PWLL41 | Nov 16 2019 | 2:00 PM | Peewee LL | Guelph Jr. Gryphons White | Exhibition | | |
| ALL31 | Nov 16 2019 | 3:00 PM | Atom LL | Guelph Jr. Gryphons Red | Exhibition | | |
| MILL27 | Nov 16 2019 | 6:30 PM | Intermediate | Cambridge Roadrunners | Woolwich Twp (St. Jacobs) | | |
| PWLL90 | Nov 17 2019 | 12:00 PM | Peewee LL | Ayr Rockets #2 | Woolwich Mem (McLeod) | | |
| ALL89 | Nov 17 2019 | 1:30 PM | Atom LL | Cambridge Roadrunners 3 | Woolwich Twp (St. Jacobs) | | |
| Nov 17 2019 | 5:30 PM | Intermediate | TBA | Woolwich Twp (St. Jacobs) | | |
| MLL113 | Nov 21 2019 | 7:30 PM | Midget LL | Grand River Mustangs 2 | Woolwich Mem (Snyder) | | |
| Nov 23 2019 | 9:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |
| ALL85 | Nov 23 2019 | 4:30 PM | Atom LL | Grand River Mustangs 1 | Woolwich Twp (St. Jacobs) | | |
| PWLL87 | Nov 23 2019 | 6:30 PM | Peewee LL | Guelph Jr. Gryphons Black | Woolwich Twp (St. Jacobs) | | |
| MILL30 | Nov 24 2019 | 6:30 PM | Intermediate | Guelph Jr. Gryphons Blue | Woolwich Twp (St. Jacobs) | | |
| MLL099 | Nov 24 2019 | 8:30 PM | Midget LL | Wilmot Wolverines 1 | Wilmot Complex (Optimist) | | |
| MLL110 | Nov 28 2019 | 7:30 PM | Midget LL | Kitchener Lady Rangers Red | Woolwich Mem (Snyder) | | |
| Nov 29-Dec 01 | Atom LL | Woolwich Wild Shootout (Elmira, Ontario) |
| Nov 29-Dec 01 | Novice LL #2 | Woolwich Shootout Tournament (Elmira, Ontario) |
| Nov 29-Dec 01 | Peewee LL | Woolwich Wild Shootout Tournament (Elmira, Ontario) |
| MILL29 | Dec 01 2019 | 6:30 PM | Intermediate | Guelph Jr. Gryphons Blue | Woolwich Twp (St. Jacobs) | | |
| MLL023 | Dec 01 2019 | 7:30 PM | Midget LL | Central Perth LL | PERC | | |
| MILL07 | Dec 06 2019 | 8:00 PM | Intermediate | Grand River Mustangs | Fergus (A) | | |
| PWLL50 | Dec 07 2019 | 1:15 PM | Peewee LL | Kitchener Lady Rangers Blue | Grand River | | |
| ALL09 | Dec 08 2019 | 10:15 AM | Atom LL | Cambridge Roadrunners 2 | Sports Park (South) | | |
| MLL073 | Dec 08 2019 | 5:00 PM | Midget LL | Waterloo Ravens #1 | Moses Springer | | |
| MILL04 | Dec 08 2019 | 9:00 PM | Intermediate | Cambridge Roadrunners | Hespeler (2) | | |
| MLL109 | Dec 12 2019 | 7:30 PM | Midget LL | Waterloo Ravens #3 | Woolwich Mem (Snyder) | | |
| MILL12 | Dec 13 2019 | 9:30 PM | Intermediate | Grand River Mustangs | Fergus (A) | | |
| Dec 14 2019 | 10:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| ALL41 | Dec 14 2019 | 1:30 PM | Atom LL | Kitchener Lady Rangers Red | Grand River | | |
| MLL107 | Dec 14 2019 | 3:30 PM | Midget LL | Wilmot Wolverines 2 | Wilmot Complex (Optimist) | | |
| PWLL89 | Dec 14 2019 | 4:30 PM | Peewee LL | Wilmot Wolverines 2 | Woolwich Twp (St. Jacobs) | | |
| Dec 27-Dec 30 | Novice LL #2 | Jason Cripps Tournament (Kitchener, Ontario) |
| Dec 27-Dec 30 | Atom LL | Jason Cripps Tournament (Kitchener, Ontario) |
| Dec 27-Dec 30 | Intermediate | Jason Cripps Tournament (Kitchener, Ontario) |
| Dec 27-Dec 30 | Peewee LL | Jason Cripps Tournament (Kitchener, Ontario) |
| Dec 27-Dec 30 | Novice LL #1 | Jason Cripps Tournament (Kitchener, Ontario) |
| Dec 27-Dec 30 | Midget LL | Jason Cripps Tournament (Kitchener, Ontario) |
| Jan 04 2020 | 9:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| Jan 04 2020 | 10:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |
| Jan 11 2020 | 9:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| Jan 17-Jan 19 | Atom LL | Brock Jr. Badgers Tournament (St. Catherines, Ontario) |
| Jan 17-Jan 19 | Novice LL #2 | Brock Jr. Badgers Tournament (St. Catharines, Ontario) |
| Jan 18 2020 | 10:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |
| Jan 18 2020 | 4:30 PM | Peewee LL | TBA | Woolwich Twp (St. Jacobs) | | |
| Feb 01 2020 | 9:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| Feb 01 2020 | 10:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |
| Feb 07-Feb 09 | Peewee LL | Stoney Creek Sweetheart Tournament (Stoney Creek, Ontario) |
| Feb 08 2020 | 9:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |
| Feb 15 2020 | 10:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| Feb 22 2020 | 9:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| Feb 22 2020 | 10:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |
| Feb 29 2020 | 9:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |
| Mar 07 2020 | 10:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| Mar 28 2020 | 9:20 AM | Novice LL #2 | TBA | Woolwich Mem (Snyder) | | |
| Mar 28 2020 | 10:20 AM | Novice LL #1 | TBA | Woolwich Mem (Snyder) | | |