| 2021-06-24 17:30:00June 24, 2021 | Douglas vs Tatnuck | 3 - 1 | Soldiers Field - Douglas | Recap | - |
| 2021-06-24 17:30:00June 24, 2021 | Holden vs Burncoat | 3 - 6 | Mountview Middle School | Recap | - |
| 2021-06-24 17:30:00June 24, 2021 | Schwartz vs South Side | 8 - 6 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2021-06-24 19:00:00June 24, 2021 | South Side vs Knights | 0 - 16 | Hadwen Park Worcester | Recap | - |
| 2021-06-25 19:00:00June 25, 2021 | Knights vs Shrewsbury | 6 - 2 | Lake Park Worcester | Recap | - |
| 2021-06-26 10:00:00June 26, 2021 | Grafton vs Holden | 4 - 3 | Grafton High School | Recap | - |
| 2021-06-26 10:00:00June 26, 2021 | Burncoat vs Douglas | 8 - 16 | Lake Park Worcester | Recap | - |
| 2021-06-26 10:00:00June 26, 2021 | Tatnuck vs Knights | 2 - 9 | Rockwood Field at Worcester State University | Recap | - |
| 2021-06-26 10:00:00June 26, 2021 | Shrewsbury vs Schwartz | 4 - 2 | Shrewsbury High School | Recap | - |
| 2021-06-26 10:00:00June 26, 2021 | South Side vs Millbury | 3 - 12 | Hadwen Park Worcester | Recap | - |
| 2021-06-27 10:00:00June 27, 2021 | Millbury vs Shrewsbury | 2 - 7 | Elmwood St. School - Millbury | Recap | - |
| 2021-06-27 10:00:00June 27, 2021 | Schwartz vs Knights | 13 - 16 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2021-06-27 10:00:00June 27, 2021 | Burncoat vs Tatnuck | 10 - 9 | Lake Park Worcester | Recap | - |
| 2021-06-27 10:00:00June 27, 2021 | Douglas vs Grafton | 15 - 3 | Soldiers Field - Douglas | Recap | - |
| 2021-06-27 11:00:00June 27, 2021 | Holden vs South Side | 15 - 3 | Mountview Middle School | Recap | - |
| 2021-06-29 17:30:00June 29, 2021 | Shrewsbury vs Holden | 6 - 4 | Shrewsbury High School | Recap | - |
| 2021-06-29 17:30:00June 29, 2021 | South Side vs Douglas | 2 - 15 | Hadwen Park Worcester | Recap | - |
| 2021-06-29 17:30:00June 29, 2021 | Tatnuck vs Schwartz | 12 - 0 | Rockwood Field at Worcester State University | Recap | - |
| 2021-06-29 19:00:00June 29, 2021 | Knights vs Millbury | 6 - 5 | Lake Park Worcester | Recap | - |
| 2021-06-30 17:30:00June 30, 2021 | Tatnuck vs Shrewsbury | 10 - 11 | Rockwood Field at Worcester State University | Recap | - |
| 2021-06-30 17:30:00June 30, 2021 | Burncoat vs Millbury | 5 - 6 | Elmwood St. School - Millbury | Recap | - |
| 2021-07-01 17:30:00July 1, 2021 | Millbury vs Schwartz | 6 - 4 | Elmwood St. School - Millbury | Recap | - |
| 2021-07-05 19:00:00July 5, 2021 | Burncoat vs South Side | 6 - 2 | Hadwen Park | Recap | - |
| 2021-07-06 17:30:00July 6, 2021 | Shrewsbury vs Burncoat | 17:30:005:30 pm | Shrewsbury High School | Recap | - |
| 2021-07-06 19:00:00July 6, 2021 | Knights vs Douglas | 6 - 17 | Lake Park Worcester | Recap | - |
| 2021-07-10 10:00:00July 10, 2021 | Knights vs Grafton | 7 - 1 | Lake Park Worcester | Recap | - |
| 2021-07-10 10:00:00July 10, 2021 | Shrewsbury vs South Side | 15 - 5 | Shrewsbury High School | Recap | - |
| 2021-07-10 10:00:00July 10, 2021 | Tatnuck vs Holden | 0 - 1 | Rockwood Field at Worcester State University | Recap | - |
| 2021-07-10 10:00:00July 10, 2021 | Schwartz vs Burncoat | 0 - 5 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2021-07-11 10:00:00July 11, 2021 | Shrewsbury vs Tatnuck | 4 - 9 | Shrewsbury High School | Recap | - |
| 2021-07-11 10:00:00July 11, 2021 | Knights vs South Side | 9 - 0 | Lake Park Worcester | Recap | - |
| 2021-07-11 10:00:00July 11, 2021 | Schwartz vs Grafton | 7 - 0 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2021-07-11 10:00:00July 11, 2021 | Millbury vs Burncoat | 2 - 5 | Elmwood St. School - Millbury | Recap | - |
| 2021-07-11 11:00:00July 11, 2021 | Holden vs Douglas | 5 - 2 | Mountview Middle School | Recap | - |
| 2021-07-12 17:30:00July 12, 2021 | Millbury vs Grafton | 17:30:005:30 pm | Elmwood St. School - Millbury | Recap | - |
| 2021-07-12 17:30:00July 12, 2021 | Schwartz vs Holden | 3 - 5 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2021-07-13 17:30:00July 13, 2021 | Tatnuck vs Douglas | 3 - 1 | Rockwood Field at Worcester State University | Recap | - |
| 2021-07-13 17:30:00July 13, 2021 | Burncoat vs Holden | 6 - 1 | Lake Park Worcester | Recap | - |
| 2021-07-13 17:30:00July 13, 2021 | Grafton vs Millbury | 5 - 1 | Grafton High School | Recap | - |
| 2021-07-13 17:30:00July 13, 2021 | South Side vs Schwartz | 2 - 13 | Hadwen Park Worcester | Recap | - |
| 2021-07-13 20:00:00July 13, 2021 | Shrewsbury vs Knights | 6 - 4 | Lake Park Worcester | Recap | - |
| 2021-07-19 17:30:00July 19, 2021 | Grafton vs Schwartz | 10 - 2 | Grafton High School | Recap | - |
| 2021-07-20 17:30:00July 20, 2021 | Holden vs Grafton | 4 - 13 | Mountview Middle School | Recap | - |
| 2021-07-20 17:30:00July 20, 2021 | Douglas vs Burncoat | 13 - 5 | Soldiers Field - Douglas | Recap | - |
| 2021-07-20 17:30:00July 20, 2021 | Schwartz vs Shrewsbury | 4 - 3 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2021-07-20 17:30:00July 20, 2021 | Millbury vs South Side | 14 - 5 | Elmwood St. School - Millbury | Recap | - |
| 2021-07-20 19:00:00July 20, 2021 | Knights vs Tatnuck | 1 - 4 | Lake Park Worcester | Recap | - |
| 2021-07-22 17:30:00July 22, 2021 | South Side vs Holden | 11 - 15 | Hadwen Park Worcester | Recap | - |
| 2021-07-22 17:30:00July 22, 2021 | Shrewsbury vs Millbury | 2 - 4 | Shrewsbury High School | Recap | - |
| 2021-07-22 17:30:00July 22, 2021 | Tatnuck vs Burncoat | 8 - 1 | Rockwood Field at Worcester State University | Recap | - |
| 2021-07-22 17:30:00July 22, 2021 | Grafton vs Douglas | 4 - 7 | Grafton High School | Recap | - |
| 2021-07-22 19:00:00July 22, 2021 | Knights vs Schwartz | 8 - 1 | Lake Park Worcester | Recap | - |
| 2021-07-24 10:00:00July 24, 2021 | Millbury vs Knights | 3 - 0 | Elmwood St. School - Millbury | Recap | - |
| 2021-07-24 10:00:00July 24, 2021 | Douglas vs South Side | 12 - 1 | Soldiers Field - Douglas | Recap | - |
| 2021-07-24 10:00:00July 24, 2021 | Burncoat vs Grafton | 14 - 10 | Lake Park Worcester | Recap | - |
| 2021-07-24 10:00:00July 24, 2021 | Schwartz vs Tatnuck | 0 - 15 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2021-07-24 11:00:00July 24, 2021 | Holden vs Shrewsbury | 2 - 17 | Mountview Middle School | Recap | - |
| 2021-07-24 12:30:00July 24, 2021 | Grafton vs Burncoat | 6 - 7 | Lake Park Worcester | Recap | - |
| 2021-07-25 10:00:00July 25, 2021 | Tatnuck vs Grafton | 13 - 7 | Rockwood Field at Worcester State University | Recap | - |
| 2021-07-25 10:00:00July 25, 2021 | Schwartz vs Millbury | 6 - 10 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2021-07-25 14:00:00July 25, 2021 | Shrewsbury vs Douglas | 4 - 3 | Soldiers Field - Douglas | Recap | - |
| 2021-07-25 16:30:00July 25, 2021 | Douglas vs Shrewsbury | 5 - 12 | Soldiers Field - Douglas | Recap | - |
| 2021-07-26 05:30:00July 26, 2021 | Holden vs Knights | 11 - 10 | Vernon Hill Park | Recap | - |
| 2021-07-26 20:00:00July 26, 2021 | Knights vs Holden | 13 - 0 | Vernon Hill Park | Recap | - |
| 2021-07-27 17:30:00July 27, 2021 | South Side vs Grafton | 17:30:005:30 pm | Hadwen Park Worcester | Recap | - |
| 2021-07-27 17:30:00July 27, 2021 | Millbury vs Tatnuck | 17:30:005:30 pm | Lake Park Worcester | Recap | - |
| 2021-07-27 17:30:00July 27, 2021 | Holden vs Schwartz | 17:30:005:30 pm | Mountview Middle School | Recap | - |
| 2021-07-27 17:30:00July 27, 2021 | Douglas vs Knights | 14 - 2 | Soldiers Field - Douglas | Recap | - |
| 2021-07-27 17:30:00July 27, 2021 | Burncoat vs Shrewsbury | 17:30:005:30 pm | Worcester State University | Recap | - |
| 2021-07-27 20:00:00July 27, 2021 | Tatnuck vs Millbury | 20:00:008:00 pm | Lake Park Worcester | Recap | - |
| 2021-07-27 20:00:00July 27, 2021 | Grafton vs South Side | 20:00:008:00 pm | Hadwen Park Worcester | Recap | - |
| 2021-07-28 17:30:00July 28, 2021 | Grafton vs Tatnuck | 17:30:005:30 pm | Grafton High School | Preview | - |
| 2021-07-28 17:30:00July 28, 2021 | Holden vs Millbury | 17:30:005:30 pm | Mountview Middle School | Preview | - |
| 2021-07-29 17:30:00July 29, 2021 | Douglas vs Schwartz | 17:30:005:30 pm | Lake Park Worcester | Preview | - |
| 2021-07-29 17:30:00July 29, 2021 | Millbury vs Holden | 17:30:005:30 pm | Elmwood St. School - Millbury | Preview | - |
| 2021-07-29 17:30:00July 29, 2021 | Tatnuck vs South Side | 17:30:005:30 pm | Rockwood Field at Worcester State University | Preview | - |
| 2021-07-29 17:30:00July 29, 2021 | Shrewsbury vs Grafton | 17:30:005:30 pm | Shrewsbury High School | Preview | - |
| 2021-07-29 17:30:00July 29, 2021 | Knights vs Burncoat | 17:30:005:30 pm | Vernon Hill Park | Preview | - |
| 2021-07-29 18:30:00July 29, 2021 | Schwartz vs Douglas | 18:30:006:30 pm | Lake Park Worcester | Preview | - |
| 2021-07-29 20:00:00July 29, 2021 | South Side vs Tatnuck | 20:00:008:00 pm | Hadwen Park Worcester | Preview | - |
| 2021-07-29 20:00:00July 29, 2021 | Burncoat vs Knights | 20:00:008:00 pm | Vernon Hill Park | Preview | - |
| 2021-07-31 10:00:00July 31, 2021 | Grafton vs Knights | 10:00:0010:00 am | Grafton High School | Preview | - |
| 2021-07-31 10:00:00July 31, 2021 | South Side vs Shrewsbury | 10:00:0010:00 am | Hadwen Park Worcester | Preview | - |
| 2021-07-31 10:00:00July 31, 2021 | Douglas vs Millbury | 10:00:0010:00 am | Soldiers Field - Douglas | Preview | - |
| 2021-07-31 10:00:00July 31, 2021 | Burncoat vs Schwartz | 10:00:0010:00 am | Lake Park Worcester | Preview | - |
| 2021-07-31 11:00:00July 31, 2021 | Holden vs Tatnuck | 11:00:0011:00 am | Mountview Middle School | Preview | - |
| 2021-08-01 10:00:00August 1, 2021 | Grafton vs Shrewsbury | 10:00:0010:00 am | Grafton High School | Preview | - |
| 2021-08-01 10:00:00August 1, 2021 | Millbury vs Douglas | 10:00:0010:00 am | Elmwood St. School - Millbury | Preview | - |
| 2021-08-01 10:00:00August 1, 2021 | South Side vs Burncoat | 10:00:0010:00 am | Hadwen Park Worcester | Preview | - |
| 2021-08-02 17:30:00August 2, 2021 | Douglas vs Holden | 17:30:005:30 pm | Soldiers Field - Douglas | Preview | - |
