Wrestler of the Year
- 2022 – Bennett Berge of Kasson-Mantorville
- 2021 – Derrick Cardinal of Forest Lake
- 2020 – Craig Orlando of Bertha-Hewitt/Verndale/Parkers Prairie
- 2019 – Greg Kerkvleit of Simley
- 2018 – Gable Steveson of Apple Valley
- 2017 – Brady Berge of Kasson-Mantorville
- 2016 – Mark Hall of Apple Valley
- 2015 – Lance Benick of Totino-Grace
- 2014 – Tommy Thorn of Saint Michael-Albertville
- 2013 – Jake Short of Simley
- 2012 – Brandon Kingsley of Apple Valley
- 2011 – Matt Kelliher of Apple Valley
- 2010 – Dylan Ness of Bloomington Kennedy
- 2009 – Kevin Steinhaus of Kerkhoven-Murdock-Sunburg
- 2008 – Jake Deitchler of Anoka
- 2007 – Zach Sanders of Wabasha-Kellogg
- 2006 – Mike Thorn of Saint Michael-Albertville
- 2005 – Nathan Matousek of Glencoe-Silver Lake
- 2004 – Charlie Falck of Apple Valley
- 2003 – Eric Sanders of Wabasha-Kellogg
Head Coach of the Year
- 2022 – Nathan Hanson of Jackson County Central
- 2021 – David Joseph of Kimball Area
- 2020 – Will Short of Simley
- 2019 – Jake Lorentz of LPGE/Browerville
- 2018 – Joe Traen of Watertown-Mayer/Mayer Lutheran
- 2017 – Link Steffen of Zumbrota-Mazeppa
- 2016 – Matt Ryan of Kenyon-Wanamingo
- 2015 – Joel Skillings of Minneota
- 2014 – Joel Viss of Chatfield
- 2013 – Dan Lefebvre of Saint Michael-Albertville
- 2012 – Will Short of Simley
- 2011 – Jim Jackson of Apple Valley
- 2010 – Jim Short and Will Short of Simley
- 2009 – Lyle Freudenburg of Foley
- 2008 – Jim Jackson of Apple Valley
- 2007 – Tim Roberg of Atwater-Cosmos-Grove City
- 2006 – Gregg Greeno of Saint Michael-Albertville
- 2005 – Mark Jenson of Pierz
- 2004 – Gregg Greeno of Saint Michael-Albertville
- 2003 – Tom Gruhlke of BOLD
Assistant Coach of the Year
- 2022 – Mike Pettit of Waconia
- 2021 – Paul Vaith of Hastings
- 2020 – Jesse Jennissen of Cambridge-Isanti
- 2019 – Lavern ‘Tuffy’ Hoard of Grand Rapids
- 2018 – Marty Aho of Frazee
- 2017 – Mark Krier of Zumbrota-Mazeppa
- 2016 – Les Engler of Minneota
- 2015 – Greg Dravis of Eastview
- 2014 – Travis Bartels of Chatfield
- 2013 – Craig Johnson of Kerkhoven-Murdock-Sunburg
- 2012 – Mark Madigan of Simley
- 2011 – Dave Pfaffinger of Blue Earth Area
- 2010 – Dwight Burman of St. James
- 2009 – Nick Fornicoia of Eastview
- 2008 – Gary Stoks of Canby
- 2007 – Bruce Rosenow of Hutchinson
- 2006 – Dan Lefebvre of Saint Michael-Albertville
- 2005 – Larry Hovden of Owatonna
- 2004 – Steve Fuchs of Paynesville Area
- 2003 – Brad Schafer of Apple Valley