| Year | # | Event | Venue | Winner |
|---|---|---|---|---|
| 2019 | 51 | Bolton Lake Regatta | Bolton Lake SC | Brangiforte, Bill |
| 2018 | 50 | Bolton Lake Regatta | Bolton Lake SC | Brangiforte, Bill |
| 2017 | 49 | Bolton Lake Regatta | Bolton Lake SC | Brangiforte, Bill |
| 2016 | 48 | Bolton Lake Regatta | Bolton Lake SC | Brangiforte, Bill |
| 2015 | 47 | Bolton Lake Regatta | Bolton Lake SC | Woodman, Eric |
| 2014 | 46 | Bolton Lake regatta | Bolton Lake SC | Brangiforte, Bill |
| 2013 | 45 | Bolton Lake Regatta | Bolton Lake SC | David, Andy |
| 2012 | 44 | Bolton Lake Regatta | Bolton Lake SC | Charles, Ken |
| 2011 | 43 | Bolton Lake Regatta | Bolton Lake SC | |
| 2010 | 42 | Bolton Lake Regatta | Bolton Lake SC | |
| 2009 | 41 | Bolton Lake Regatta | Bolton Lake SC | Brangiforte, Bill |
| 2008 | 40 | Bolton Lake Regatta | Bolton Lake SC | Langford, Steve |
| 2007 | 39 | Bolton Lake Regatta | Bolton Lake SC | Brangiforte, Bill |
| 2006 | 38 | Bolton Lake Regatta | Bolton Lake SC | Brangiforte, Bill |
| 2005 | 37 | Bolton Lake Regatta | Bolton Lake SC | |
| 2004 | 36 | Bolton Lake Regatta | Bolton Lake SC | Buttner, Drew |
| 2003 | 35 | Bolton Lake Regatta | Bolton Lake SC | |
| 2002 | 34 | Bolton Lake Regatta | Bolton Lake SC | Catalano, Michael |
| 2001 | 33 | Bolton Lake Regatta | Bolton Lake SC | Buttner, Drew |
| 2000 | 32 | Bolton Lake Regatta | Bolton Lake SC | Edwards-Swan, Anne |
| 1999 | 31 | Bolton Lake Regatta | Bolton Lake SC | Catalano, Michael |
| 1998 | 30 | Bolton Lake Regatta | Bolton Lake SC | Dickinson, Malcolm |
| 1997 | 29 | Bolton Lake Regatta | Bolton Lake SC | Buttner, Drew |
| 1996 | 28 | Bolton Lake Regatta | Bolton Lake SC | Buttner, Drew |
| 1995 | 27 | Bolton Lake Regatta | Bolton Lake SC | Buttner, Drew |
| 1994 | 26 | Bolton Lake Regatta | Bolton Lake SC | Davies, David |
| 1993 | 25 | Bolton Lake Regatta | Bolton Lake SC | Dickinson, Malcolm |
| 1992 | 24 | Bolton Lake Regatta | Bolton Lake SC | |
| 1991 | 23 | Bolton Lake Regatta | Bolton Lake SC | Woodman, Eric |
| 1990 | 22 | Bolton Lake Regatta | Bolton Lake SC | Heckman, Bob |
| 1989 | 21 | Bolton Lake Regatta | Bolton Lake SC | Friend, Chris |
| 1988 | 20 | Bolton Lake Regatta | Bolton Lake SC | |
| 1987 | 19 | Bolton Lake Regatta | Bolton Lake SC | |
| 1986 | 19 | Bolton Lake Regatta | Bolton Lake SC | Greenbaum, Scott |
| 1985 | 17 | Bolton Lake Regatta | Bolton Lake SC | |
| 1984 | 16 | Bolton Lake Regatta | Bolton Lake SC | Greenbaum, Scott |
| 1983 | 15 | Bolton Lake Regatta | Bolton Lake SC | |
| 1982 | 14 | Bolton Lake Regatta | Bolton Lake SC | Boll, William |
| 1981 | 13 | Bolton Lake Regatta | Bolton Lake SC | |
| 1980 | 12 | Bolton Lake Regatta | Bolton Lake SC | |
| 1979 | 11 | Bolton Lake Regatta | Bolton Lake SC |