| 09/12/2023 | Auburn | Dudley Coach Pitch Softball | 5:30PM - 6:30PM | Dudley - Crawford Field / Softball |
| 09/21/2023 | Dudley Coach Pitch Softball | Auburn | 5:30PM - 6:30PM | Auburn - Lemansky Park / Senior Baseball |
| 09/28/2023 | Dudley Coach Pitch Softball | Sturbridge (Coach Katie) | 5:30PM - 6:30PM | Sturbridge Burgess Elementary / Burgess Upper Softball |
| 10/03/2023 | Dudley Coach Pitch Softball | Auburn | 5:30PM - 6:30PM | Auburn - Pappas Recreation Complex / Softball |
| 10/04/2023 | Dudley Coach Pitch Softball | Sturbridge (Coach Chris) | 5:30PM - 6:30PM | Sturbridge Burgess Elementary / Burgess Upper Softball |
| 10/06/2023 | Dudley Coach Pitch Softball | Webster | 5:30PM - 6:30PM | Webster - Slater Street / Field 1 |
| 10/11/2023 | Sturbridge (Coach Chris) | Dudley Coach Pitch Softball | 5:30PM - 6:30PM | Dudley - Crawford Field / Softball |
| 10/19/2023 | Sturbridge (Coach Katie) | Dudley Coach Pitch Softball | 5:30PM - 6:30PM | Dudley - Crawford Field / Softball |
| 10/20/2023 | Webster | Dudley Coach Pitch Softball | 5:30PM - 6:30PM | Dudley - Crawford Field / Softball |
| 10/27/2023 | Webster | Dudley Coach Pitch Softball | 5:30PM - 6:30PM | Dudley - Crawford Field / Softball |