Optimist Blue Season Championship
| Year |
Skipper |
Club |
| 2023 |
Ainsley Zagol |
NESS |
| 2022 |
Kate Van Berkel |
NESS |
| 2021 |
Coby Fagan |
Niantic Bay |
| 2020 |
COVID Pandemic |
No Results |
| 2019 |
Ike Schutz |
NESS |
| 2018 |
Ike Schutz |
Sachems Head |
| 2017 |
Harvey DeMovick |
WHYC / NESS / MudRatz |
| 2016 |