| Date | Time | Type | Home School | Away School | Site |
| TUE 9/9 | 3:30 PM | League | North Yarmouth Academy | Waynflete | NYA, Poulin Family Tennis Courts |
| THU 9/11 | 3:30 PM | League | Cape Elizabeth Middle School | North Yarmouth Academy | Cape Elizabeth |
| TUE 9/16 | 3:30 PM | League | North Yarmouth Academy | Freeport | NYA, Poulin Family Tennis Courts |
| WED 9/24 | Canceled | League | Greely Middle | North Yarmouth Academy | Greely |
| THU 9/25 | Canceled | League | Waynflete | North Yarmouth Academy | Waynflete Sports Complex |
| TUE 9/30 | 3:30 PM | League | North Yarmouth Academy | Cape Elizabeth Middle School | NYA, Poulin Family Tennis Courts |
| WED 10/1 | 3:30 PM | League | Freeport | North Yarmouth Academy | Freeport |
| MON 10/6 | 3:30 PM | League | Greely Middle | North Yarmouth Academy | Val Halla Golf & Recreation Center |
| TUE 10/7 | 3:30 PM | League | Harrison Middle School - Yarmouth | North Yarmouth Academy | Yarmouth |
| THU 10/9 | 3:30 PM | League | North Yarmouth Academy | Greely Middle | NYA, Poulin Family Tennis Courts |
| TUE 10/14 | 3:30 PM | League | Waynflete | North Yarmouth Academy | Waynflete Sports Complex |
| WED 10/15 | 3:30 PM | League | North Yarmouth Academy | Cape Elizabeth Middle School | NYA, Poulin Family Tennis Courts |
| TUE 10/21 | 3:30 PM | League | North Yarmouth Academy | Freeport | NYA, Poulin Family Tennis Courts |
| THU 10/23 | 3:30 PM | League | Waynflete | North Yarmouth Academy | Waynflete Sports Complex |
| MON 10/27 | 3:30 PM | League | North Yarmouth Academy | Harrison Middle School - Yarmouth | NYA, Poulin Family Tennis Courts |