| 2023-06-03 10:00:00June 3, 2023 | Schwartz vs Douglas | 10:00:0010:00 am | Joe Schwartz Babe Ruth Field | Recap | - |
| 2023-06-03 10:00:00June 3, 2023 | Shrewsbury vs Tatnuck | 3 - 4 | Lake Park Worcester | Recap | - |
| 2023-06-03 10:00:00June 3, 2023 | Shrewsbury vs Millbury | 10:00:0010:00 am | Shrewsbury High School | Recap | - |
| 2023-06-03 10:00:00June 3, 2023 | Vernon Hill vs Tatnuck | 10:00:0010:00 am | Lake Park Worcester | Recap | - |
| 2023-06-04 10:00:00June 4, 2023 | Shrewsbury vs Schwartz | 0 - 2 | Lake Park Worcester | Recap | - |
| 2023-06-04 10:00:00June 4, 2023 | Douglas vs Tatnuck | 10:00:0010:00 am | Soldiers Field - Douglas | Recap | - |
| 2023-06-04 10:00:00June 4, 2023 | Millbury vs South Side | 10:00:0010:00 am | Elmwood St. School - Millbury | Recap | - |
| 2023-06-06 17:30:00June 6, 2023 | Millbury vs Vernon Hill | 17:30:005:30 pm | Elmwood St. School - Millbury | Recap | - |
| 2023-06-06 18:00:00June 6, 2023 | Schwartz vs Tatnuck | 5 - 15 | Lake Park Worcester | Recap | - |
| 2023-06-06 18:00:00June 6, 2023 | South Side vs Douglas | 18:00:006:00 pm | Hadwen Park Worcester | Recap | - |
| 2023-06-08 17:30:00June 8, 2023 | Douglas vs Millbury | 17:30:005:30 pm | Soldiers Field - Douglas | Preview | - |
| 2023-06-08 17:30:00June 8, 2023 | Shrewsbury vs South Side | 17:30:005:30 pm | Shrewsbury High School | Preview | - |
| 2023-06-08 18:00:00June 8, 2023 | Vernon Hill vs Schwartz | 18:00:006:00 pm | Lake Park Worcester | Preview | - |
| 2023-06-10 10:00:00June 10, 2023 | Tatnuck vs South Side | 10:00:0010:00 am | Worcester State University | Preview | - |
| 2023-06-10 10:00:00June 10, 2023 | Schwartz vs Millbury | 10:00:0010:00 am | Joe Schwartz Babe Ruth Field | Preview | - |
| 2023-06-10 10:00:00June 10, 2023 | Shrewsbury vs Vernon Hill | 10:00:0010:00 am | Lake Park Worcester | Preview | - |
| 2023-06-11 10:00:00June 11, 2023 | Vernon Hill vs South Side | 10:00:0010:00 am | Lake Park Worcester | Preview | - |
| 2023-06-11 10:00:00June 11, 2023 | Tatnuck vs Millbury | 10:00:0010:00 am | Worcester State University | Preview | - |
| 2023-06-11 10:00:00June 11, 2023 | Douglas vs Shrewsbury | 10:00:0010:00 am | Soldiers Field - Douglas | Preview | - |
| 2023-06-11 12:30:00June 11, 2023 | Vernon Hill vs South Side | 12:30:0012:30 pm | Lake Park Worcester | Preview | - |
| 2023-06-13 17:30:00June 13, 2023 | Schwartz vs South Side | 17:30:005:30 pm | Joe Schwartz Babe Ruth Field | Preview | - |
| 2023-06-13 17:30:00June 13, 2023 | Tatnuck vs Shrewsbury | 17:30:005:30 pm | Worcester State University | Preview | - |
| 2023-06-13 18:00:00June 13, 2023 | Vernon Hill vs Douglas | 18:00:006:00 pm | Lake Park Worcester | Preview | - |
| 2023-06-15 17:30:00June 15, 2023 | Tatnuck vs Vernon Hill | 17:30:005:30 pm | Worcester State University | Preview | - |
| 2023-06-15 17:30:00June 15, 2023 | Douglas vs Schwartz | 17:30:005:30 pm | Soldiers Field - Douglas | Preview | - |
| 2023-06-15 17:30:00June 15, 2023 | Shrewsbury vs Millbury | 17:30:005:30 pm | Lake Park Worcester | Preview | - |
| 2023-06-15 20:00:00June 15, 2023 | Shrewsbury vs Millbury | 20:00:008:00 pm | Lake Park Worcester | Preview | - |
| 2023-06-17 10:00:00June 17, 2023 | South Side vs Millbury | 10:00:0010:00 am | Hadwen Park Worcester | Preview | - |
| 2023-06-17 10:00:00June 17, 2023 | Tatnuck vs Douglas | 10:00:0010:00 am | Worcester State University | Preview | - |
| 2023-06-17 10:00:00June 17, 2023 | Schwartz vs Shrewsbury | 10:00:0010:00 am | Lake Park Worcester | Preview | - |
| 2023-06-17 13:00:00June 17, 2023 | Tatnuck vs Douglas | 13:00:001:00 pm | Worcester State University | Preview | - |
| 2023-06-18 10:00:00June 18, 2023 | Tatnuck vs Schwartz | 10:00:0010:00 am | Worcester State University | Preview | - |
| 2023-06-18 10:00:00June 18, 2023 | Vernon Hill vs Millbury | 10:00:0010:00 am | Lake Park Worcester | Preview | - |
| 2023-06-18 10:00:00June 18, 2023 | Douglas vs South Side | 10:00:0010:00 am | Soldiers Field - Douglas | Preview | - |
| 2023-06-20 17:30:00June 20, 2023 | South Side vs Shrewsbury | 17:30:005:30 pm | Hadwen Park Worcester | Preview | - |
| 2023-06-20 17:30:00June 20, 2023 | Schwartz vs Vernon Hill | 17:30:005:30 pm | Lake Park Worcester | Preview | - |
| 2023-06-20 17:30:00June 20, 2023 | Millbury vs Douglas | 17:30:005:30 pm | Elmwood St. School - Millbury | Preview | - |
| 2023-06-20 20:00:00June 20, 2023 | Schwartz vs Vernon Hill | 20:00:008:00 pm | Lake Park Worcester | Preview | - |
| 2023-06-22 17:30:00June 22, 2023 | South Side vs Tatnuck | 17:30:005:30 pm | Hadwen Park Worcester | Preview | - |
| 2023-06-22 17:30:00June 22, 2023 | Millbury vs Schwartz | 17:30:005:30 pm | Elmwood St. School - Millbury | Preview | - |
| 2023-06-22 18:00:00June 22, 2023 | Vernon Hill vs Shrewsbury | 18:00:006:00 pm | Lake Park Worcester | Preview | - |
| 2023-06-22 20:00:00June 22, 2023 | South Side vs Tatnuck | 20:00:008:00 pm | Hadwen Park Worcester | Preview | - |
| 2023-06-24 10:00:00June 24, 2023 | Shrewsbury vs Douglas | 10:00:0010:00 am | Lake Park Worcester | Preview | - |
| 2023-06-24 10:00:00June 24, 2023 | Millbury vs Tatnuck | 10:00:0010:00 am | Elmwood St. School - Millbury | Preview | - |
| 2023-06-24 10:00:00June 24, 2023 | South Side vs Vernon Hill | 10:00:0010:00 am | Hadwen Park Worcester | Preview | - |
| 2023-06-25 10:00:00June 25, 2023 | Douglas vs Vernon Hill | 10:00:0010:00 am | Soldiers Field - Douglas | Preview | - |
| 2023-06-25 10:00:00June 25, 2023 | South Side vs Schwartz | 10:00:0010:00 am | Hadwen Park Worcester | Preview | - |
| 2023-06-27 17:30:00June 27, 2023 | Tatnuck vs Vernon Hill | 17:30:005:30 pm | Worcester State University | Preview | - |
| 2023-06-27 17:30:00June 27, 2023 | Millbury vs Shrewsbury | 17:30:005:30 pm | Elmwood St. School - Millbury | Preview | - |
| 2023-06-27 18:00:00June 27, 2023 | Schwartz vs Douglas | 18:00:006:00 pm | Lake Park Worcester | Preview | - |
| 2023-06-29 17:30:00June 29, 2023 | Douglas vs Tatnuck | 17:30:005:30 pm | Soldiers Field - Douglas | Preview | - |
| 2023-06-29 18:00:00June 29, 2023 | South Side vs Millbury | 18:00:006:00 pm | Hadwen Park Worcester | Preview | - |
| 2023-06-29 18:00:00June 29, 2023 | Shrewsbury vs Schwartz | 18:00:006:00 pm | Lake Park Worcester | Preview | - |
