| 2023-06-03 10:00:00June 3, 2023 | Shrewsbury vs Tatnuck | 4 - 3 | Lake Park Worcester | Recap | - |
| 2023-06-04 10:00:00June 4, 2023 | Millbury vs South Side | 3 - 1 | Elmwood St. School - Millbury | Recap | - |
| 2023-06-04 10:00:00June 4, 2023 | Shrewsbury vs Schwartz | 2 - 0 | Lake Park Worcester | Recap | - |
| 2023-06-06 17:30:00June 6, 2023 | Millbury vs Vernon Hill | 2 - 6 | Elmwood St. School - Millbury | Recap | - |
| 2023-06-06 18:00:00June 6, 2023 | South Side vs Douglas | 13 - 2 | Hadwen Park Worcester | Recap | - |
| 2023-06-06 18:00:00June 6, 2023 | Schwartz vs Tatnuck | 15 - 5 | Lake Park Worcester | Recap | - |
| 2023-06-08 17:30:00June 8, 2023 | Shrewsbury vs South Side | 2 - 5 | Shrewsbury High School | Recap | - |
| 2023-06-08 18:00:00June 8, 2023 | Vernon Hill vs Schwartz | 6 - 0 | Lake Park Worcester | Recap | - |
| 2023-06-10 10:00:00June 10, 2023 | Schwartz vs Douglas | 1 - 2 | Soldiers Field - Douglas | Recap | - |
| 2023-06-10 10:00:00June 10, 2023 | Shrewsbury vs Vernon Hill | 6 - 15 | Lake Park Worcester | Recap | - |
| 2023-06-10 10:00:00June 10, 2023 | Tatnuck vs South Side | 0 - 13 | Worcester State University | Recap | - |
| 2023-06-11 10:00:00June 11, 2023 | Vernon Hill vs South Side | 0 - 7 | Lake Park Worcester | Recap | - |
| 2023-06-11 10:00:00June 11, 2023 | Douglas vs Shrewsbury | 4 - 6 | Shrewsbury High School | Recap | - |
| 2023-06-11 12:30:00June 11, 2023 | Vernon Hill vs South Side | 4 - 15 | Lake Park Worcester | Recap | - |
| 2023-06-12 17:30:00June 12, 2023 | Schwartz vs Millbury | 0 - 10 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2023-06-13 17:30:00June 13, 2023 | Schwartz vs South Side | 7 - 11 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2023-06-13 17:30:00June 13, 2023 | Tatnuck vs Shrewsbury | 6 - 4 | Worcester State University | Recap | - |
| 2023-06-13 18:00:00June 13, 2023 | Vernon Hill vs Douglas | 0 - 3 | Lake Park Worcester | Recap | - |
| 2023-06-15 17:30:00June 15, 2023 | Douglas vs Schwartz | 5 - 3 | Soldiers Field - Douglas | Recap | - |
| 2023-06-15 17:30:00June 15, 2023 | Tatnuck vs Vernon Hill | 3 - 15 | Worcester State University | Recap | - |
| 2023-06-15 20:00:00June 15, 2023 | Shrewsbury vs Millbury | 3 - 4 | Lake Park Worcester | Recap | - |
| 2023-06-17 10:00:00June 17, 2023 | South Side vs Millbury | 13 - 1 | Hadwen Park Worcester | Recap | - |
| 2023-06-18 10:00:00June 18, 2023 | Douglas vs South Side | 3 - 19 | Soldiers Field - Douglas | Recap | - |
| 2023-06-18 10:00:00June 18, 2023 | Tatnuck vs Schwartz | 2 - 7 | Worcester State University | Recap | - |
| 2023-06-19 19:00:00June 19, 2023 | Schwartz vs Vernon Hill | 1 - 0 | Vernon Hill Park | Recap | - |
| 2023-06-20 17:30:00June 20, 2023 | Millbury vs Douglas | 6 - 2 | Elmwood St. School - Millbury | Recap | - |
| 2023-06-20 17:30:00June 20, 2023 | South Side vs Shrewsbury | 14 - 8 | Hadwen Park Worcester | Recap | - |
| 2023-06-20 17:30:00June 20, 2023 | Schwartz vs Vernon Hill | 4 - 8 | Lake Park Worcester | Recap | - |
| 2023-06-21 17:30:00June 21, 2023 | Vernon Hill vs Tatnuck | 16 - 3 | Vernon Hill Park | Recap | - |
| 2023-06-21 17:30:00June 21, 2023 | Douglas vs Millbury | 1 - 5 | Millbury Jr/Sr HS | Recap | - |
| 2023-06-22 17:30:00June 22, 2023 | Millbury vs Schwartz | 4 - 3 | Elmwood St. School - Millbury | Recap | - |
| 2023-06-22 17:30:00June 22, 2023 | South Side vs Tatnuck | 13 - 4 | Hadwen Park Worcester | Recap | - |
| 2023-06-22 18:00:00June 22, 2023 | Vernon Hill vs Shrewsbury | 4 - 6 | Lake Park Worcester | Recap | - |
| 2023-06-22 20:00:00June 22, 2023 | South Side vs Tatnuck | 21 - 4 | Hadwen Park Worcester | Recap | - |
| 2023-06-23 17:30:00June 23, 2023 | Douglas vs Tatnuck | 2 - 0 | Worcester State University | Recap | - |
| 2023-06-23 17:30:00June 23, 2023 | Schwartz vs Shrewsbury | 11 - 6 | Joe Schwartz Babe Ruth Field | Recap | - |
| 2023-06-24 10:00:00June 24, 2023 | South Side vs Vernon Hill | 12 - 1 | Hadwen Park Worcester | Recap | - |
| 2023-06-24 10:00:00June 24, 2023 | Shrewsbury vs Douglas | 8 - 7 | Lake Park Worcester | Recap | - |
| 2023-06-24 13:30:00June 24, 2023 | Tatnuck vs Douglas | 0 - 9 | Soldiers Field | Recap | - |
| 2023-06-25 10:00:00June 25, 2023 | Shrewsbury vs Millbury | 7 - 6 | Lake Park Worcester | Recap | - |
| 2023-06-25 10:00:00June 25, 2023 | South Side vs Schwartz | 13 - 1 | Hadwen Park Worcester | Recap | - |
| 2023-06-25 10:00:00June 25, 2023 | Douglas vs Vernon Hill | 0 - 6 | Soldiers Field - Douglas | Recap | - |
| 2023-06-25 12:30:00June 25, 2023 | Shrewsbury vs Millbury | 10 - 9 | Lake Park Worcester | Recap | - |
| 2023-06-26 17:30:00June 26, 2023 | Millbury vs Tatnuck | 8 - 2 | Tivnan Field | Recap | - |
| 2023-06-27 17:30:00June 27, 2023 | Millbury vs Shrewsbury | 15 - 5 | Elmwood St. School - Millbury | Recap | - |
| 2023-06-27 17:30:00June 27, 2023 | Tatnuck vs Vernon Hill | 1 - 20 | Worcester State University | Recap | - |
| 2023-06-27 18:00:00June 27, 2023 | Schwartz vs Douglas | 2 - 1 | Lake Park Worcester | Recap | - |
| 2023-06-28 17:30:00June 28, 2023 | Tatnuck vs Millbury | 1 - 9 | Worcester State University | Recap | - |
| 2023-06-29 17:30:00June 29, 2023 | Douglas vs Tatnuck | 5 - 3 | Vernon Hill Park | Recap | - |
| 2023-06-29 18:00:00June 29, 2023 | South Side vs Millbury | 6 - 1 | Hadwen Park Worcester | Recap | - |
| 2023-06-29 18:00:00June 29, 2023 | Shrewsbury vs Schwartz | 10 - 3 | Lake Park Worcester | Recap | - |
| 2023-06-29 19:45:00June 29, 2023 | Tatnuck vs Douglas | 8 - 9 | Vernon Hill | Recap | - |
| 2023-07-01 10:00:00July 1, 2023 | Vernon Hill vs Millbury | 1 - 6 | Lake Park Worcester | Recap | - |
