| 07/11/2019 | JF10 Lunenburg | JF10 Leominster American | 5:30PM - 7:30PM | Ronnie Bachand Memorial Field / Field A | |
| 07/11/2019 | JF10 Quabbin | JF10 Leominster National | 5:30PM - 7:30PM | Angelo Picucci Memorial Field / Major League Field | |
| 07/13/2019 | JF11 Chuck Stone | JF11 North Leominster | 1:00PM - 3:00PM | Justin DeSantis Field / Major League Field | |
| 07/13/2019 | JF11 Lunenburg | JF11 Quabbin | 1:00PM - 3:00PM | Felton Field-Barre / Felton 1 | |
| 07/15/2019 | JF10 North Leominster | JF10 Lunenburg | 5:30PM - 7:30PM | Marshall Park / Powell Field | |
| 07/15/2019 | JF10 Leominster National | JF10 Leominster American | 5:30PM - 7:30PM | Ronnie Bachand Memorial Field / Field A | |
| 07/16/2019 | JF11 North Leominster | JF11 Quabbin | 5:30PM - 7:30PM | Felton Field-Barre / Felton 1 | |
| 07/16/2019 | JF11 Chuck Stone | JF11 Lunenburg | 5:30PM - 7:30PM | Marshall Park / Powell Field | |
| 07/18/2019 | JF10 Quabbin | JF10 North Leominster | 5:30PM - 7:30PM | Justin DeSantis Field / Major League Field | |
| 07/18/2019 | JF10 Leominster National | JF10 Lunenburg | 5:30PM - 7:30PM | Marshall Park / Powell Field | |
| 07/20/2019 | JF11 Lunenburg | JF11 North Leominster | 1:00PM - 3:00PM | Justin DeSantis Field / Major League Field | |
| 07/20/2019 | JF11 Quabbin | JF11 Chuck Stone | 1:00PM - 3:00PM | Salevan Field / Salevan Field | |
| 07/21/2019 | JF10 North Leominster | JF10 Leominster National | 1:00PM - 3:00PM | Angelo Picucci Memorial Field / Major League Field | |
| 07/21/2019 | JF10 Leominster American | JF10 Quabbin | 1:00PM - 3:00PM | Felton Field-Barre / Felton 1 | |
| 07/23/2019 | JF11 North Leominster | JF11 Chuck Stone | 5:30PM - 7:30PM | Salevan Field / Salevan Field | |
| 07/23/2019 | JF11 Quabbin | JF11 Lunenburg | 5:30PM - 7:30PM | Marshall Park / Powell Field | |
| 07/24/2019 | JF10 Leominster American | JF10 North Leominster | 5:30PM - 7:30PM | Justin DeSantis Field / Major League Field | |
| 07/24/2019 | JF10 Lunenburg | JF10 Quabbin | 5:30PM - 7:30PM | Felton Field-Barre / Felton 1 | |
| 07/26/2019 | JF11 Quabbin | JF11 North Leominster | 5:30PM - 7:30PM | Justin DeSantis Field / Major League Field | |
| 07/26/2019 | JF11 Lunenburg | JF11 Chuck Stone | 5:30PM - 7:30PM | Salevan Field / Salevan Field | |
| 07/29/2019 | JF11 North Leominster | JF11 Lunenburg | 5:30PM - 7:30PM | Marshall Park / Powell Field | |
| 07/29/2019 | JF11 Chuck Stone | JF11 Quabbin | 5:30PM - 7:30PM | Felton Field-Barre / Felton 1 | |