| 2019-06-08 10:00:00June 8, 2019 | Holden vs Burncoat | 9 - 5 | Mountview Middle School | Recap | - |
| 2019-06-08 10:00:00June 8, 2019 | Shrewsbury vs Millbury (PPD) | 10:00:0010:00 am | Shrewsbury High School | Recap | - |
| 2019-06-09 10:00:00June 9, 2019 | Burncoat vs Douglas | 4 - 10 | Soldiers Field - Douglas | Recap | - |
| 2019-06-09 10:00:00June 9, 2019 | Schwartz vs Double Play | 0 - 7 | Lake Park Worcester | Recap | - |
| 2019-06-09 10:00:00June 9, 2019 | Millbury vs Oxford | 7 - 6 | Millbury Jr/Sr HS | Recap | - |
| 2019-06-11 12:30:00June 11, 2019 | Double Play vs Holden | 16 - 14 | Lake Park Worcester | Recap | - |
| 2019-06-11 17:45:00June 11, 2019 | Schwartz vs Oxford | 4 - 5 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2019-06-11 17:45:00June 11, 2019 | Tatnuck vs Burncoat | 3 - 0 | Worcester State University | Recap | - |
| 2019-06-13 17:45:00June 13, 2019 | Holden vs Oxford | 7 - 0 | Mountview Middle School | Recap | - |
| 2019-06-15 10:00:00June 15, 2019 | Douglas vs Holden | 11 - 10 | Soldiers Field - Douglas | Recap | - |
| 2019-06-15 10:00:00June 15, 2019 | Oxford vs Burncoat | 13 - 3 | Oxford High School | Recap | - |
| 2019-06-15 10:00:00June 15, 2019 | Double Play vs Millbury | 3 - 6 | Vernon Hill Park | Recap | - |
| 2019-06-16 10:00:00June 16, 2019 | Burncoat vs Millbury | 0 - 7 | Aaron Krock Field | Recap | - |
| 2019-06-16 10:00:00June 16, 2019 | Holden vs Schwartz | 6 - 10 | Mountview Middle School | Recap | - |
| 2019-06-16 10:00:00June 16, 2019 | Tatnuck vs Oxford | 2 - 5 | Worcester State University | Recap | - |
| 2019-06-17 17:45:00June 17, 2019 | Douglas vs Millbury | 14 - 9 | Millbury Jr/Sr HS, Soldiers Field - Douglas | Recap | - |
| 2019-06-18 17:45:00June 18, 2019 | Schwartz vs Burncoat | 13 - 3 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2019-06-18 17:45:00June 18, 2019 | Oxford vs Shrewsbury | 17:45:005:45 pm | Oxford High School | Recap | - |
| 2019-06-19 17:45:00June 19, 2019 | Millbury vs Tatnuck | 2 - 7 | Millbury Jr/Sr HS | Recap | - |
| 2019-06-19 17:45:00June 19, 2019 | Oxford vs Double Play | 9 - 8 | Oxford High School | Recap | - |
| 2019-06-19 17:45:00June 19, 2019 | Shrewsbury vs Holden | 7 - 5 | Shrewsbury High School | Recap | - |
| 2019-06-20 17:30:00June 20, 2019 | Burncoat vs Double Play | 3 - 6 | Tivnan Field at Lake Park | Recap | - |
| 2019-06-20 17:45:00June 20, 2019 | Schwartz vs Shrewsbury | 6 - 1 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2019-06-20 17:45:00June 20, 2019 | Millbury vs Holden | 2 - 9 | Millbury Jr/Sr HS | Recap | - |
| 2019-06-20 17:45:00June 20, 2019 | Oxford vs Douglas | 5 - 1 | Oxford High School | Recap | - |
| 2019-06-20 20:00:00June 20, 2019 | Double Play vs Tatnuck | 7 - 17 | Tivnan Field at Lake Park | Recap | - |
| 2019-06-22 10:00:00June 22, 2019 | Schwartz vs Douglas | 9 - 2 | Aaron Krock Field | Recap | - |
| 2019-06-22 10:00:00June 22, 2019 | Tatnuck vs Millbury | 7 - 6 | Lake Park Worcester | Recap | - |
| 2019-06-22 13:00:00June 22, 2019 | Double Play vs Oxford | 0 - 11 | Lake Park Worcester | Recap | - |
| 2019-06-22 15:30:00June 22, 2019 | Burncoat vs Shrewsbury | 6 - 7 | Lake Park Worcester | Recap | - |
| 2019-06-23 10:00:00June 23, 2019 | Double Play vs Douglas | 5 - 8 | Soldiers Field - Douglas | Recap | - |
| 2019-06-23 10:00:00June 23, 2019 | Schwartz vs Tatnuck | 0 - 2 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2019-06-23 10:00:00June 23, 2019 | Burncoat vs Holden | 1 - 18 | Lake Park Worcester | Recap | - |
| 2019-06-23 10:00:00June 23, 2019 | Millbury vs Shrewsbury | 5 - 6 | Millbury Jr/Sr HS | Recap | - |
| 2019-06-23 12:30:00June 23, 2019 | Double Play vs Douglas | 9 - 10 | Soldiers Field - Douglas | Recap | - |
| 2019-06-23 12:30:00June 23, 2019 | Schwartz vs Tatnuck | 0 - 15 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2019-06-23 12:30:00June 23, 2019 | Burncoat vs Holden | 6 - 11 | Lake Park Worcester | Recap | - |
| 2019-06-23 12:30:00June 23, 2019 | Millbury vs Shrewsbury | 2 - 6 | Millbury Jr/Sr HS | Recap | - |
| 2019-06-24 05:45:00June 24, 2019 | Tatnuck vs Schwartz | 13 - 1 | Vernon Hill Park | Recap | - |
| 2019-06-25 17:30:00June 25, 2019 | Double Play vs Schwartz | 2 - 13 | Tivnan Field at Lake Park | Recap | - |
| 2019-06-25 17:45:00June 25, 2019 | Oxford vs Millbury | 3 - 18 | Oxford High School | Recap | - |
| 2019-06-25 19:00:00June 25, 2019 | Douglas vs Burncoat | 8 - 3 | Vernon Hill Park | Recap | - |
| 2019-06-26 17:30:00June 26, 2019 | Holden vs Tatnuck | 3 - 10 | Mountview Middle School | Recap | - |
| 2019-06-26 17:45:00June 26, 2019 | Schwartz vs Douglas | 4 - 0 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2019-06-26 19:00:00June 26, 2019 | Shrewsbury vs Burncoat | 7 - 3 | Vernon Hill Park | Recap | - |
| 2019-06-27 17:30:00June 27, 2019 | Double Play vs Douglas | 5 - 1 | Lake Park Worcester | Recap | - |
| 2019-06-27 17:30:00June 27, 2019 | Oxford vs Schwartz | 1 - 11 | Greenbrier Park Oxford | Recap | - |
| 2019-06-27 17:45:00June 27, 2019 | Millbury vs Douglas | 10 - 8 | Millbury Jr/Sr HS | Recap | - |
| 2019-06-27 17:45:00June 27, 2019 | Holden vs Shrewsbury | 0 - 6 | Mountview Middle School | Recap | - |
| 2019-06-27 20:00:00June 27, 2019 | Oxford vs Schwartz | 4 - 2 | Greenbrier Park Oxford | Recap | - |
| 2019-06-27 20:00:00June 27, 2019 | Burncoat vs Tatnuck | 0 - 13 | Lake Park Worcester | Recap | - |
| 2019-06-29 10:00:00June 29, 2019 | Douglas vs Shrewsbury | 2 - 10 | Soldiers Field - Douglas | Recap | - |
| 2019-06-29 10:00:00June 29, 2019 | Schwartz vs Millbury | 3 - 9 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2019-06-29 10:00:00June 29, 2019 | Double Play vs Burncoat | 12 - 1 | Lake Park Worcester | Recap | - |
| 2019-06-29 10:00:00June 29, 2019 | Oxford vs Holden | 1 - 7 | Oxford High School | Recap | - |
| 2019-06-29 12:30:00June 29, 2019 | Shrewsbury vs Douglas | 8 - 6 | Soldiers Field - Douglas | Recap | - |
| 2019-06-30 10:00:00June 30, 2019 | Burncoat vs Oxford | 7 - 0 | Lake Park Worcester | Recap | - |
| 2019-06-30 10:00:00June 30, 2019 | Double Play vs Millbury | 7 - 1 | Millbury Jr/Sr HS | Recap | - |
| 2019-06-30 10:00:00June 30, 2019 | Holden vs Douglas | 3 - 9 | Mountview Middle School | Recap | - |
| 2019-06-30 10:00:00June 30, 2019 | Shrewsbury vs Tatnuck | 2 - 5 | Shrewsbury High School | Recap | - |
| 2019-06-30 12:30:00June 30, 2019 | Burncoat vs Oxford | 7 - 0 | Lake Park Worcester | Recap | - |
| 2019-06-30 12:30:00June 30, 2019 | Double Play vs Millbury | 8 - 1 | Millbury Jr/Sr HS | Recap | - |
| 2019-06-30 12:30:00June 30, 2019 | Holden vs Douglas | 10 - 5 | Mountview Middle School | Recap | - |
| 2019-06-30 12:30:00June 30, 2019 | Shrewsbury vs Tatnuck | 0 - 9 | Shrewsbury High School | Recap | - |
| 2019-07-01 17:45:00July 1, 2019 | Millbury vs Schwartz | 10 - 6 | Millbury Jr/Sr HS | Recap | - |
| 2019-07-01 17:45:00July 1, 2019 | Tatnuck vs Shrewsbury | 5 - 4 | Shrewsbury High School | Recap | - |
| 2019-07-02 17:30:00July 2, 2019 | Double Play vs Shrewsbury | 10 - 8 | Lake Park Worcester | Recap | - |
| 2019-07-02 17:45:00July 2, 2019 | Schwartz vs Holden | 9 - 4 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2019-07-02 17:45:00July 2, 2019 | Millbury vs Burncoat | 13 - 1 | Millbury Jr/Sr HS | Recap | - |
| 2019-07-02 17:45:00July 2, 2019 | Oxford vs Tatnuck | 2 - 5 | Oxford High School | Recap | - |
| 2019-07-02 20:00:00July 2, 2019 | Shrewsbury vs Double Play | 11 - 1 | Tivnan Field at Lake Park | Recap | - |
| 2019-07-05 17:45:00July 5, 2019 | Tatnuck vs Holden | 9 - 6 | Worcester State University | Recap | - |
| 2019-07-06 10:00:00July 6, 2019 | Holden vs Double Play | 0 - 7 | Mountview Middle School | Recap | - |
| 2019-07-06 10:00:00July 6, 2019 | Burncoat vs Schwartz | 0 - 11 | Lake Park Worcester | Recap | - |
| 2019-07-06 10:00:00July 6, 2019 | Shrewsbury vs Oxford | 13 - 1 | Shrewsbury High School | Recap | - |
| 2019-07-06 10:00:00July 6, 2019 | Tatnuck vs Douglas | 7 - 5 | Worcester State University | Recap | - |
| 2019-07-06 11:30:00July 6, 2019 | Douglas vs Tatnuck | 3 - 2 | Rockwood Field @ Worcester State University | Recap | - |
| 2019-07-07 10:00:00July 7, 2019 | Douglas vs Oxford | 1 - 12 | Soldiers Field - Douglas | Recap | - |
| 2019-07-07 10:00:00July 7, 2019 | Holden vs Millbury | 4 - 3 | Mountview Middle School | Recap | - |
| 2019-07-07 10:00:00July 7, 2019 | Shrewsbury vs Schwartz | 3 - 2 | Shrewsbury High School | Recap | - |
| 2019-07-07 10:00:00July 7, 2019 | Tatnuck vs Double Play | 19 - 4 | Worcester State University | Recap | - |
| 2019-07-09 17:30:42July 9, 2019 | Playoffs 1st Rd Game 1 - #5 Millbury vs. #4 Schwartz | 4 - 6 | Tivnan Field at Lake Park | Recap | - |
| 2019-07-09 20:00:02July 9, 2019 | Playoffs 1st Rd Game 2 - #6 Holden vs. #3 Double Play | 8 - 6 | Tivnan Field at Lake Park | Recap | - |
| 2019-07-11 17:30:52July 11, 2019 | Playoffs - Semi-finals - # 5 Millbury vs. # 2 Shrewsbury | 0 - 3 | Tivnan Field at Lake Park | Recap | - |
| 2019-07-11 20:00:04July 11, 2019 | Playoffs - Semi-finals - # 6 Holden vs. # 1 Tatnuck | 1 - 0 | Tivnan Field at Lake Park | Recap | - |
| 2019-07-13 10:00:07July 13, 2019 | Playoffs - Championship Series Game 1 - Holden vs. Schrewsbury | 10:00:0710:00 am | Tivnan Field at Lake Park | Recap | - |
| 2019-07-13 12:30:38July 13, 2019 | Championship Series Game 2 - Holden vs. Shrewsbury | 12:30:3812:30 pm | Tivnan Field at Lake Park | Recap | - |
