Awarded to the best maintained J/105 that takes part in the International Masters and/or Lipton Cup regatta
| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2024 | Bennett Greenwald | Perseverance | ||
| 2023 | Bill Quealy | J Rabbit Slim | ||
| 2022 | Elena & John Bennett | Boss Lady | ||
| 2021 | Scott Lowry | Ohana | ||
| 2019 | Richad & Cyndy Collins | Lucky Duck | ||
| 2018 | Donica & Scott Ryder | Sanity | ||
| 2017 | Jeff & Karen Brown | sweet karen | ||
| 2016 | Diane Speidelli | Ondine | ||
| 2015 | Annette Matthies | Hibiscus | ||
| 2014 | Dennis & Sharon Case | Wings | ||
| 2013 | Stewart Cannon | J-OK |