Awarded on Opening Day to the Best Maintained PC Class.
| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2022-2024 | Neil Ledsam | Adios | ||
| 2021 | Chris & Dale Frost | Blue Chip | ||
| 2019 | Joyce & Phillip Thearle | Adios | ||
| 2016-2017 | Chris Frost | Blue Chip | ||
| 2015 | Richard Pavelec | Dawn | ||
| 2013 | Steve Brownsea | Zest | ||
| 2012 | John Dodge & Doug Holthaus | Celeste | ||
| 2010 | Vance & Lois Gustafson | Jade | ||
| 2009 | Doug Holthaus | Celeste | ||
| 2008 | Diane Scheider & Dave Grundies | Yankee | ||
| 2007 | S/C Betty Sherman & Carl M. Eichenlaub | |||
| 2005-2006 | Rich Pavelec | Dawn | ||
| 2004 | George Lindley & Gary Gould & Geves Kenny | La Cucaracha | ||
| 2000 | Rich Pavelec | Puff | ||
| 1999 | Blake Oversmith | Tradewind | ||
| 1998 | Rich Pavelec | Puff | ||
| 1997 | Gene Trepte | Waterwagon | ||
| 1973 | Joe Gann | Kaos | ||
| 1970-1971 | Adm. J.R. McKnight | Severn | ||
| 1965-1969 | George B. Harris III | Interlude | ||
| 1964 | Frank Hope | Esperance | ||
| 1962-1963 | Jack Bone | Skylark | ||
| 1955-1956 | E.G. Ellsworth | Sea Lur | ||
| 1953-1954 | E.B. Ellsworth | Sea Lur | ||
| 1952 | Harold Amrein | Marianne | ||
| 1951 | R.W. vanWart | Six Bits | ||
| 1950 | E. Tobin | Spirit | ||
| 1949 | Tom Cross | Lady Jean | ||
| 1948 | John Fox | Zorra | ||
| 1947 | Herbert Richard | Vici | ||
| 1945 | T. Eckels | Velero | ||
| 1944 | John Fox | Zorra | ||
| 1941 | Roger Bryan | Mynx | ||
| 1940 | Stanley Christopher | Velero |