| 09/07/2019 | Monroe-Woodbury 1 | Junior Baseball | 3:30PM - 6:00PM | Wallkill Area Little League / Senior | |
| 09/14/2019 | Junior Baseball | New Windsor | 3:30PM - 6:00PM | New Windsor Little League / Senior | |
| 09/21/2019 | Minisink Black | Junior Baseball | 3:30PM - 6:00PM | Wallkill Area Little League / Senior | |
| 09/28/2019 | Junior Baseball | Minisink Black | 3:30PM - 6:00PM | Otisville Little League / Field A | |
| 10/05/2019 | Junior Baseball | Washingtonville | 1:00PM - 3:30PM | Washingtonville Little League / 60X90 | |
| 10/12/2019 | New Windsor | Junior Baseball | 1:00PM - 3:30PM | Wallkill Area Little League / Senior | |