| 04/17/2021 | Navy | Red | 9:00AM - 11:15AM | Wallkill Area Little League / Major | |
| 04/17/2021 | Mets | Giants | 9:00AM - 11:15AM | Town of Newburgh Little League / 4 | |
| 04/17/2021 | Royal | Grey | 11:30AM - 1:45PM | Wallkill Area Little League / Batting Cage | |
| 04/17/2021 | Dodgers | Yankees | 11:30AM - 1:45PM | Town of Newburgh Little League / 4 | |
| 04/20/2021 | Yankees | Royal | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 04/20/2021 | Red | Mets | 5:45PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 04/21/2021 | Giants | Dodgers | 5:45PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 04/22/2021 | Navy | Grey | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 04/24/2021 | Grey | Red | 9:00AM - 11:15AM | Wallkill Area Little League / Major | |
| 04/24/2021 | Yankees | Giants | 9:00AM - 11:15AM | Town of Newburgh Little League / 4 | |
| 04/24/2021 | Royal | Navy | 11:30AM - 1:45PM | Wallkill Area Little League / Batting Cage | |
| 04/24/2021 | Dodgers | Mets | 11:30AM - 1:45PM | Town of Newburgh Little League / 4 | |
| 04/27/2021 | Red | Navy | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 04/27/2021 | Giants | Mets | 5:45PM - 9:00PM | New Windsor Little League / NWLL Maj | |
| 04/28/2021 | Yankees | Dodgers | 5:45PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 04/29/2021 | Grey | Royal | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 05/01/2021 | Yankees | Navy | 9:00AM - 11:15AM | Wallkill Area Little League / Major | |
| 05/01/2021 | Royal | Mets | 9:00AM - 11:15AM | Town of Newburgh Little League / 4 | |
| 05/01/2021 | Dodgers | Red | 11:30AM - 1:45PM | Wallkill Area Little League / Batting Cage | |
| 05/01/2021 | Grey | Giants | 11:30AM - 1:45PM | Town of Newburgh Little League / 4 | |
| 05/04/2021 | Grey | Royal | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 05/04/2021 | Giants | Mets | 6:00PM - 9:00PM | New Windsor Little League / NWLL Maj | |
| 05/06/2021 | Red | Navy | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 05/06/2021 | Yankees | Dodgers | 6:00PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 05/08/2021 | Red | Royal | 9:00AM - 11:15AM | Wallkill Area Little League / Major | |
| 05/08/2021 | Giants | Dodgers | 9:00AM - 11:15AM | Town of Newburgh Little League / 4 | |
| 05/08/2021 | Navy | Grey | 11:30AM - 1:45PM | Wallkill Area Little League / Batting Cage | |
| 05/08/2021 | Mets | Yankees | 11:30AM - 1:45PM | Town of Newburgh Little League / 4 | |
| 05/11/2021 | Giants | Red | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 05/11/2021 | Royal | Dodgers | 6:00PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 05/12/2021 | Grey | Yankees | 6:00PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 05/13/2021 | Mets | Navy | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 05/15/2021 | Red | Royal | 9:00AM - 11:15AM | Wallkill Area Little League / Major | |
| 05/15/2021 | Mets | Yankees | 9:00AM - 11:15AM | Town of Newburgh Little League / 4 | |
| 05/15/2021 | Dodgers | Grey | 11:30AM - 1:45PM | Wallkill Area Little League / Batting Cage | |
| 05/15/2021 | Navy | Giants | 11:30AM - 1:45PM | Town of Newburgh Little League / 4 | |
| 05/18/2021 | Grey | Red | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 05/18/2021 | Yankees | Giants | 6:00PM - 9:00PM | New Windsor Little League / NWLL Maj | |
| 05/19/2021 | Dodgers | Mets | 6:00PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 05/20/2021 | Royal | Navy | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 05/22/2021 | Mets | Grey | 9:00AM - 11:15AM | Wallkill Area Little League / Major | |
| 05/22/2021 | Red | Yankees | 9:00AM - 11:15AM | Town of Newburgh Little League / 4 | |
| 05/22/2021 | Giants | Royal | 11:30AM - 1:45PM | Wallkill Area Little League / Major | |
| 05/22/2021 | Navy | Dodgers | 11:30AM - 1:45PM | Town of Newburgh Little League / 4 | |
| 05/25/2021 | Grey | Navy | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 05/25/2021 | Yankees | Mets | 6:00PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 05/26/2021 | Dodgers | Giants | 6:00PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 05/27/2021 | Royal | Red | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 06/01/2021 | Navy | Royal | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 06/01/2021 | Giants | Yankees | 6:00PM - 9:00PM | New Windsor Little League / NWLL Maj | |
| 06/03/2021 | Red | Grey | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 06/03/2021 | Mets | Dodgers | 6:00PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 06/05/2021 | Navy | Red | 9:00AM - 11:15AM | Wallkill Area Little League / Major | |
| 06/05/2021 | Mets | Giants | 9:00AM - 11:15AM | Town of Newburgh Little League / 4 | |
| 06/05/2021 | Royal | Grey | 11:30AM - 1:45PM | Wallkill Area Little League / Batting Cage | |
| 06/05/2021 | Dodgers | Yankees | 11:30AM - 1:45PM | Town of Newburgh Little League / 4 | |
| 06/08/2021 | Grey | Navy | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 06/08/2021 | Yankees | Mets | 6:00PM - 9:00PM | New Windsor Little League / NWLL Maj | |
| 06/10/2021 | Royal | Red | 5:45PM - 9:00PM | Wallkill Area Little League / Major | |
| 06/10/2021 | Dodgers | Giants | 6:00PM - 9:00PM | Town of Newburgh Little League / 4 | |
| 06/12/2021 | Navy | Royal | 9:00AM - 11:15AM | Wallkill Area Little League / Major | |
| 06/12/2021 | Mets | Dodgers | 9:00AM - 11:15AM | Town of Newburgh Little League / 4 | |
| 06/12/2021 | Red | Grey | 11:30AM - 1:45PM | Wallkill Area Little League / Batting Cage | |
| 06/12/2021 | Giants | Yankees | 11:30AM - 1:45PM | Town of Newburgh Little League / 4 | |