Charles Maier Trophy
This trophy shall be awarded each year to the Class X Junior fleet yacht skippered in all official races during the regatta by a girl who has the highest position for the full regatta as recordedby the current official scoring system of the ILYA in competition with other girl skippers in the regatta.
| Year | Name of Boat | Club | Skipper |
| 1979 | Magpie II | Beaver Lake Yacht Club | Margaret Friend |
| 1980 | Rattler | Pine Lake Yacht Club | Annie Kotovic |
| 1981 | Pirate | Pewaukee Yacht Club | Eliza Meyer |
| 1982 | Dreamboat | Pewaukee Yacht Club | Sally Sawyer |
| 1983 | Gone with the Wind | Pine Lake Yacht Club | Leisl Rickmeier |
| 1984 | Good | Pewaukee Yacht Club | Debbie Schieble |
| 1985 | Little Me | Cedar Lake Yacht Club | Cathy McGowan |
| 1986 | Pier Pressure | Cedar Lake Yacht Club | Amy Dukes |
| 1987 | Wave Cutter | Delavan Lake Yacht Club | Jennifer Herz |
| 1988 | Esprit | Cedar Lake Yacht Club | Cheri Tews |
| 1989 | Think Fast | Pewaukee Yacht Club | Kara Krause |
| 1990 | Hiking Heidi | Cedar Lake Yacht Club | Heidi Lieber |
| 1991 | No Pain-No Gain | Lac LaBelle Yacht Club | Barb Keck |
| 1992 | Spilly | Pine Lake Yacht Club | Sally Barkow |
| 1993 | Spilly | Pine Lake Yacht Club | Sally Barkow |
| 1994 | Spilly | Pine Lake Yacht Club | Sally Barkow |
| 1995 | Class of 99 | Pewaukee Yacht Club | Kaitlin Krause |
| 1996 | Cub Fans | Delavan Lake Yacht Club | Diana Szczepanski |
| 1997 | More Magic | Minnetonka Yacht Club | Lindsay Allen |
| 1998 | Carefully Sailing | Pine lake Yacht Club | Carrie Petri |
| 1999 | Speed Bump | Cedar Lake Yacht Club | Patti Schmidt |
| 2000 | Speed Bump | Cedar Lake Yacht Club | Patti Schmidt |
| 2001 | Fiddis | Lake Beulah Yacht Club | Annie Kate Haeger |
| 2002 | Fiddis | Lake Beulah Yacht Club | Annie Kate Haeger |
| 2003 | Fiddis | Lake Beulah Yacht Club | Annie Kate Haeger |
| 2004 | Qtr Pounder w/Small Fry Cedar Lake Yacht Club | Becky Schmidt | |
| 2005 | Sweet Sailin’ | Okauchee Yacht Club | Shannon Smith |
| 2006 | Starfish | Minnetonka Yacht Club | Addy Ferguson |
| 2007 | Starfish | Minnetonka Yacht Club | Addy Ferguson |
| 2008 | Starfish | Minnetonka Yacht Club | Addy Ferguson |
| 2009 | Hamma Tine | Lake Beulah Yacht Club | Mary Claire Kiernan |
| 2010 | Regatta incomplete – Lack of wind | ||
| 2011 | Twizzler | White Bear Yacht Club | Kate Cox |
| 2012 | Twizzler | White Bear Yacht Club | Kate Cox |
| 2013 | All Is On | Delavan Lake Yacht Club | Allison Marozza |
| 2014 | Barr-B-Que | Lake Beulah Yacht Club | Brigit Barr |
| 2015 | Barr-B-Que | Lake Beulah Yacht Club | Brigit Barr |
| 2016 | Classified | Cedar Lake Yacht Club | Brittany Shabino |
| 2017 | Simonized | Pewaukee Lake Yacht Club | Meta Simon |
| 2018 | Swag Diva | Pewaukee Lake Yacht Club | Ella Schieble |
| 2019 | Lolo | Minnetonka Yacht Club | Lauren Strothman |
| 2020 | Vamanos Toast | Lake Geneva Yacht Club | Annie Samis |
| 2021 | Extreme Sisterpower | Lake Geneva Yacht Club | Sophie Niemann |
Photo Credit: Melges Performance Sailboats| Morgan Kinney
Annie Samis and Nissa Berman