| 04/30/2019 | Elks | Dragons | 5:30PM - 7:30PM | Leppenen Field / Leppanen Baseball | |
| 04/30/2019 | Fisher | Lions | 5:30PM - 7:30PM | Thomaston Athletic Field / Thomaston LL Field | |
| 05/02/2019 | Dragons | Fisher | 5:30PM - 7:30PM | Gordon Field / Gordon Baseball | |
| 05/02/2019 | Elks | Lions | 6:30PM - 8:30PM | Thomaston Athletic Field / Thomaston LL Field | |
| 05/04/2019 | Lions | Ravens | 11:00AM - 1:00PM | Vinalhaven School / Vinalhaven School Field | |
| 05/04/2019 | Dragons | Elks | 1:00PM - 3:00PM | Gordon Field / Gordon Baseball | |
| 05/04/2019 | Lions | Ravens | 1:00PM - 3:00PM | Vinalhaven School / Vinalhaven School Field | |
| 05/07/2019 | Elks | Fisher | 5:30PM - 7:30PM | Gordon Field / Gordon Baseball | |
| 05/07/2019 | Lions | Dragons | 5:30PM - 7:30PM | Leppenen Field / Leppanen Baseball | |
| 05/09/2019 | Fisher | Dragons | 5:30PM - 7:30PM | Leppenen Field / Leppanen Baseball | |
| 05/09/2019 | Lions | Elks | 5:30PM - 7:30PM | Gordon Field / Gordon Baseball | |
| 05/11/2019 | Elks | Ravens | 9:00AM - 11:00AM | Gordon Field / Gordon Baseball | |
| 05/11/2019 | Ravens | Elks | 12:00PM - 2:00PM | Gordon Field / Gordon Baseball | |
| 05/16/2019 | Elks | Fisher | 5:30PM - 7:30PM | Gordon Field / Gordon Baseball | |
| 05/16/2019 | Dragons | Lions | 6:30PM - 8:30PM | Thomaston Athletic Field / Thomaston LL Field | |
| 05/18/2019 | Ravens | Fisher | 9:00AM - 11:00AM | Gordon Field / Gordon Baseball | |
| 05/18/2019 | Fisher | Ravens | 12:00PM - 2:00PM | Gordon Field / Gordon Baseball | |
| 05/18/2019 | Lions | Elks | 3:00PM - 5:00PM | Gordon Field / Gordon Baseball | |
| 05/21/2019 | Elks | Dragons | 5:30PM - 7:30PM | Leppenen Field / Leppanen Baseball | |
| 05/21/2019 | Fisher | Lions | 7:00PM - 9:00PM | Thomaston Athletic Field / Thomaston LL Field | |
| 05/25/2019 | Ravens | Dragons | 9:00AM - 11:00AM | Leppenen Field / Leppanen Baseball | |
| 05/25/2019 | Dragons | Ravens | 12:00PM - 2:00PM | Leppenen Field / Leppanen Baseball | |
| 05/30/2019 | Dragons | Fisher | 5:30PM - 7:30PM | Gordon Field / Gordon Baseball | |
| 06/01/2019 | Ravens | Lions | 9:00AM - 11:00AM | Thomaston Athletic Field / Thomaston LL Field | |
| 06/01/2019 | Ravens | Elks | 12:00PM - 2:00PM | Thomaston Athletic Field / Thomaston LL Field | |
| 06/04/2019 | Lions | Fisher | 5:30PM - 7:30PM | Gordon Field / Gordon Baseball | |
| 06/06/2019 | Fisher | Elks | 5:30PM - 7:30PM | Gordon Field / Gordon Baseball | Rescheduled |
| 06/08/2019 | Ravens | Fisher | 9:00AM - 11:00AM | Gordon Field / Gordon Baseball | |
| 06/08/2019 | Lions | Dragons | 9:00AM - 11:00AM | Thomaston Athletic Field / Thomaston LL Field | Rescheduled |
| 06/08/2019 | Dragons | Ravens | 12:00PM - 2:00PM | Gordon Field / Gordon Baseball | |