| 05/16/2026 | Northstars | Hannaford | 11:00AM - 1:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 05/16/2026 | Police | Hillside IGA | 11:00AM - 1:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 05/16/2026 | Knights | S.W. Collins | 1:00PM - 3:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 05/16/2026 | MVH/VFW | White Smiles | 1:00PM - 3:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 05/18/2026 | Sleeper's | Machias Savings Bank | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 05/19/2026 | Machias Savings Bank | White Smiles | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 05/19/2026 | Sleeper's | Knights | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 05/20/2026 | Hannaford | MVH/VFW | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 05/20/2026 | Police | Northstars | 6:00PM - 8:00PM | Stockholm Little League Field / John Anderson Memorial Field | |
| 05/21/2026 | Hillside IGA | S.W. Collins | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 05/22/2026 | MVH/VFW | Northstars | 6:00PM - 8:00PM | Stockholm Little League Field / John Anderson Memorial Field | |
| 05/25/2026 | White Smiles | S.W. Collins | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | Postponed |
| 05/27/2026 | Machias Savings Bank | Northstars | 6:00PM - 8:00PM | Stockholm Little League Field / John Anderson Memorial Field | |
| 05/29/2026 | Hillside IGA | Sleeper's | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 05/29/2026 | Machias Savings Bank | MVH/VFW | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 05/30/2026 | Hannaford | Police | 10:00AM - 12:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 05/30/2026 | MVH/VFW | Hillside IGA | 10:00AM - 12:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 05/30/2026 | White Smiles | Northstars | 11:00AM - 1:00PM | Stockholm Little League Field / John Anderson Memorial Field | |
| 06/01/2026 | Sleeper's | Police | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/01/2026 | Knights | Machias Savings Bank | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/03/2026 | S.W. Collins | Hannaford | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/04/2026 | S.W. Collins | Police | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/05/2026 | Knights | MVH/VFW | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/05/2026 | Northstars | Sleeper's | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/05/2026 | White Smiles | Hillside IGA | 6:00PM - 8:00PM | Fort Fairfield Little League Field / Field 1 | |
| 06/06/2026 | MVH/VFW | Sleeper's | 10:00AM - 12:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/06/2026 | Machias Savings Bank | Hannaford | 10:00AM - 12:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/06/2026 | Knights | Police | 12:00PM - 2:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/08/2026 | S.W. Collins | Machias Savings Bank | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/08/2026 | Northstars | Hillside IGA | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/09/2026 | White Smiles | Hannaford | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/10/2026 | Knights | Northstars | 6:00PM - 8:00PM | Stockholm Little League Field / John Anderson Memorial Field | |
| 06/11/2026 | S.W. Collins | MVH/VFW | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/11/2026 | Sleeper's | White Smiles | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/12/2026 | Hillside IGA | Hannaford | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/12/2026 | S.W. Collins | Northstars | 6:00PM - 8:00PM | Stockholm Little League Field / John Anderson Memorial Field | |
| 06/13/2026 | White Smiles | Knights | 10:00AM - 12:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/15/2026 | Police | MVH/VFW | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/16/2026 | Hannaford | Knights | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/16/2026 | Police | White Smiles | 6:00PM - 8:00PM | Fort Fairfield Little League Field / Field 1 | |
| 06/17/2026 | Northstars | Machias Savings Bank | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/17/2026 | Sleeper's | S.W. Collins | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/18/2026 | White Smiles | MVH/VFW | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/18/2026 | Hillside IGA | Knights | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/19/2026 | Machias Savings Bank | Police | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/20/2026 | Machias Savings Bank | Sleeper's | 10:00AM - 12:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/20/2026 | Northstars | MVH/VFW | 10:00AM - 12:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/20/2026 | Hannaford | Hillside IGA | 10:00AM - 12:00PM | Fort Fairfield Little League Field / Field 1 | |
| 06/22/2026 | S.W. Collins | Knights | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/22/2026 | Hillside IGA | Police | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/23/2026 | Hannaford | Sleeper's | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/23/2026 | White Smiles | Machias Savings Bank | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/24/2026 | Police | Knights | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/24/2026 | Hannaford | S.W. Collins | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/25/2026 | MVH/VFW | Machias Savings Bank | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/25/2026 | White Smiles | Sleeper's | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/25/2026 | Knights | Hillside IGA | 6:00PM - 8:00PM | Fort Fairfield Little League Field / Field 1 | |
| 06/27/2026 | Police | S.W. Collins | 10:00AM - 12:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/29/2026 | Northstars | White Smiles | 6:00PM - 8:00PM | Fort Fairfield Little League Field / Field 1 | |
| 06/30/2026 | Knights | Hannaford | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 06/30/2026 | Sleeper's | MVH/VFW | 6:00PM - 8:00PM | Hilltop Little League Complex / ROTARY FIELD | |
| 06/30/2026 | S.W. Collins | Hillside IGA | 6:00PM - 8:00PM | Fort Fairfield Little League Field / Field 1 | |
| 07/01/2026 | Hillside IGA | Machias Savings Bank | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 07/02/2026 | Police | Hannaford | 6:00PM - 8:00PM | Hilltop Little League Complex / WHITE FIELD | |
| 07/02/2026 | Sleeper's | Northstars | 6:00PM - 8:00PM | Stockholm Little League Field / John Anderson Memorial Field | |