| 09/09/2023 | Bunt Force Trauma | Southern Delmarva Baseball | 11:00AM - 12:40PM | Delmarva Pony League / Main Field |
| 09/09/2023 | Southern Delmarva Baseball | Bunt Force Trauma | 1:00PM - 2:40PM | Delmarva Pony League / Main Field |
| 09/10/2023 | Blue Crabs | Loring | 1:00PM - 2:40PM | Delmarva Pony League / Main Field |
| 09/10/2023 | Loring | Blue Crabs | 3:00PM - 4:40PM | Delmarva Pony League / Main Field |
| 09/11/2023 | Southern Delmarva Baseball | Easton | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 09/11/2023 | Easton | Southern Delmarva Baseball | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 09/14/2023 | Blue Crabs | Weaver | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 09/14/2023 | Weaver | Blue Crabs | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 09/16/2023 | Loring | Bunt Force Trauma | 11:00AM - 12:40PM | Delmarva Pony League / Main Field |
| 09/16/2023 | Bunt Force Trauma | Loring | 1:00PM - 2:40PM | Delmarva Pony League / Main Field |
| 09/18/2023 | Loring | Southern Delmarva Baseball | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 09/18/2023 | Southern Delmarva Baseball | Loring | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 09/20/2023 | Blue Crabs | Easton | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 09/20/2023 | Easton | Blue Crabs | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 09/21/2023 | Bunt Force Trauma | Weaver | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 09/21/2023 | Weaver | Bunt Force Trauma | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 09/25/2023 | Blue Crabs | Southern Delmarva Baseball | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 09/25/2023 | Southern Delmarva Baseball | Blue Crabs | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 09/27/2023 | Weaver | Loring | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 09/27/2023 | Loring | Weaver | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 09/28/2023 | Bunt Force Trauma | Easton | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 09/28/2023 | Easton | Bunt Force Trauma | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 10/04/2023 | Easton | Southern Delmarva Baseball | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 10/04/2023 | Southern Delmarva Baseball | Easton | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 10/05/2023 | Blue Crabs | Weaver | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 10/05/2023 | Weaver | Blue Crabs | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 10/11/2023 | Blue Crabs | Bunt Force Trauma | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 10/11/2023 | Bunt Force Trauma | Blue Crabs | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 10/12/2023 | Weaver | Southern Delmarva Baseball | 5:50PM - 7:30PM | Delmarva Pony League / Main Field |
| 10/12/2023 | Southern Delmarva Baseball | Weaver | 7:50PM - 9:30PM | Delmarva Pony League / Main Field |
| 10/24/2023 | Easton | Weaver | 6:00PM - 8:00PM | Delmarva Pony League / Main Field |