The Back Bay Skippers started as a single class club, building and racing AMYA Soling 1 Meter class boats in 2008. Starting in 2010, the current perpetual trophy was awarded to the skipper with the best overall score for the season, to keep for one year. Rules have changed over the years about how the scores are calculated, and what is the minimum number of regattas a skipper must have competed in to be considered for the award. No award was given for the 2020 season, which was not scored due to the pandemic.
Champions
- 2008 – Anthony Quinn
- 2009 –
- 2010 – Ned Lakeman
- 2011 – Ned Lakeman
- 2012 – Ned Lakeman
- 2013 – Ned Lakeman
- 2014 – Tim Wright
- 2015 – Tim Wright
- 2016 – Tim Wright
- 2017 – Tim Wright
- 2018 – Tim Wright
- 2019 – Tim Wright
- 2020 – (not awarded)
- 2021 – Tim Wright
- 2022 – Tim Wright
- 2023 – Tim Wright
- 2024 – Tim Wright
- 2025 – Tim Wright