| 09/20/2023 | Redmen Orioles | Rotary Club-Wicomico Reds | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 09/22/2023 | Pohanka Phillies | East Salisbury Pirates | 5:45PM - 8:00PM | East Wicomico Little League / Field 3 | |
| 09/27/2023 | Rotary Club-Wicomico Reds | East Salisbury Pirates | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 09/29/2023 | Pohanka Phillies | Rotary Club-Wicomico Reds | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/02/2023 | Redmen Orioles | East Salisbury Pirates | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/04/2023 | Rotary Club-Wicomico Reds | Redmen Orioles | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/06/2023 | East Salisbury Pirates | Pohanka Phillies | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/09/2023 | Redmen Orioles | Pohanka Phillies | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/11/2023 | East Salisbury Pirates | Rotary Club-Wicomico Reds | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/13/2023 | Rotary Club-Wicomico Reds | Pohanka Phillies | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/16/2023 | Pohanka Phillies | East Salisbury Pirates | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/17/2023 | Pohanka Phillies | Redmen Orioles | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | Rescheduled |
| 10/18/2023 | East Salisbury Pirates | Redmen Orioles | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/20/2023 | Redmen Orioles | Rotary Club-Wicomico Reds | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/23/2023 | Pohanka Phillies | Redmen Orioles | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/24/2023 | East Salisbury Pirates | Redmen Orioles | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | Rescheduled |
| 10/25/2023 | Rotary Club-Wicomico Reds | East Salisbury Pirates | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/27/2023 | Pohanka Phillies | Rotary Club-Wicomico Reds | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 10/30/2023 | East Salisbury Pirates | Pohanka Phillies | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 11/01/2023 | Rotary Club-Wicomico Reds | Redmen Orioles | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 11/03/2023 | Redmen Orioles | East Salisbury Pirates | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | |
| 11/07/2023 | Rotary Club-Wicomico Reds | Pohanka Phillies | 6:00PM - 8:00PM | Fruitland Little League / Field 1 - Harkins Yard | Canceled |