LLHL MOST GENTLEMANLY PLAYERS
| Year | Player | Team |
| 1978 - 79 | Ross Ruedig | Drake |
| 1979 - 80 | Ross Ruedig | Drake |
| 1980 - 81 | Glen Leggot | Lanigan |
| 1981 - 82 | Ross Ruedig | Drake |
| 1982 - 83 | Ross Ruedig | Drake |
| 1983 - 84 | Lorne Bartel | Drake |
| 1984 - 85 | Ken Koenig | Simpson |
| 1985 - 86 | Ken Harding | Watrous |
| 1986 - 87 | Ross Ruedig | Drake |
| 1987 - 88 | Al Faford | Simpson |
| 1988 - 89 | Curtis Wacker | Jansen |
| 1989 - 90 | Pat Mooney | Imperial |
| 1990 - 91 | Ward Snell/Gary Dietrich/Troy Stenson | Watrous/LeRoy/Lanigan |
| 1991 - 92 | Pat Mooney | Imperial |
| 1992 - 93 | Dan Johnson | Watrous |
| 1993 - 94 | James Munroe | Nokomis |
| 1994 - 95 | Dustin Halstead | Nokomis |
| 1995 - 96 | Mike Merk | Nokomis |
| 1996 - 97 | Barry Smith | Drake |
| 1997 - 98 | Barry Smith | Drake |
| 1998 - 99 | Derek Gross | Watrous |
| 1999 - 00 | Trent Bryksa/Jason Zimmerman | Lanigan/LeRoy |
| 2000 - 01 | Lindsay Holt | Watrous |
| 2001 - 02 | Dan Rauckman | LeRoy |
| 2002 - 03 | Therrin Wallin | Drake |
| 2003 - 04 | Therrin Wallin | Drake |
| 2004 - 05 | Trevor Winkler/Dan Rauckman | Lanigan/LeRoy |
| 2005 - 06 | Trent Bryksa | Lanigan |
| 2006 - 07 | Mike Bubnick | Watrous |
| 2007 - 08 | Jade Hine | Nokomis |
| 2008 - 09 | Brett McRuvie | Lanigan |
| 2009 - 10 | Josh Sim | Davidson |
| 2010 - 11 | Dean Beuker | Lanigan |