| Year | # | Event | Venue | Winner |
|---|---|---|---|---|
| 2019 | 0 | Midwest Regional #2 | Hueston SA | Norton, Dan |
| 2018 | 0 | Midwest Regional | Devils Lake YC | Norton, Dan |
| 2016 | 0 | Highland Park Mayors Cup/MW Regional | North Shore YC | Chapman, Rich |
| 2015 | 0 | Midwest Regional #1 | Wawasee YC | Gauger, Derek |
| 2015 | 0 | Midwest Regional #2 | Devils Lake YC | Norton, Dan |
| 2009 | 0 | Midwest Regional #1 | Lake Bluff YC | Chapman, Rich |
| 2008 | 65 | This One's For Fun/ MW Regional | Devils Lake YC | Fries, Derrick |
| 2007 | 0 | Midwest Regional #1 | Douglas Lake | Fries, Derrick |
| 2007 | 0 | Midwest Regional #2 | Lake Bluff YC | Chapman, Rich |
| 2007 | 64 | This One's For Fun/ MW Regional | Devils Lake YC | Norton, Dan |
| 2006 | 0 | Midwest Regional #1 | Lake Wawasee YC | Tillman, Dick |
| 2006 | 63 | This One's For Fun/ MW Regional | Devils Lake YC | Norton, Dan |
| 2005 | 62 | This One's For Fun/ MW Regional | Devils Lake YC | Norton, Dan |
| 2005 | 0 | Midwest Regional #1 | Hueston SA | Fries, Derrick |
| 2004 | 0 | Midwest Regional #2 | Lake Bliff YC | Chapman, Rich |
| 2004 | 0 | Midwest Regional #3 | Wawasee YC | Norton, Dan |
| 2004 | 0 | Midwest Regional #1 | Hueston SA | Chapman, Rich |
| 2003 | 0 | Midwest Regional #1 | Lake Bluff YC | Herndon, Eric |
| 2003 | 0 | Midwest Regional #2 | Wawasee YC | Chapman, Rich |
| 2002 | 0 | Midwest Regional #1 | Pymatuning SC | Fries, Derrick |
| 2001 | 0 | Midwest Regional #2 | Devils Lake YC | Fries, Derrick |
| 2001 | 0 | Midwest Regional #1 | Springfield YC | Feldman, Dan |
| 2000 | 0 | Midwest Regional #2 | Highland Park | Chapman, Rich |
| 1999 | 0 | Midwest Regional #2 | Devils Lake YC | Fries, Derrick |
| 1999 | 0 | Midwest Regional #1 | Island Bay YC | Feldman, Dan |
| 1998 | 0 | Midwest Regional | Lake Bluff YC | Lowrie, Chris |
| 1997 | 0 | Midwest Regional #1 | Kentucky Lake SC | Liebl, James |
| 1997 | 0 | Midwest Regional #2 | Indian Lake, OH | Liebl, James |
| 1996 | 0 | Midwest Regional | Winnetka YC | Liebl, James |
| 1995 | 0 | Midwest Regional | Lake Bluff YC | Findlay, Bob |
| 1995 | 0 | Midwest Regional #2 | Macatawa Bay YC | Tillman, Linda |
| 1994 | 0 | Midwest Regional | Clark Lake YC | Bergman, Jean |
| 1994 | 0 | Midwest Regional #2 | North Shore YC | Findlay, Bob |
| 1992 | 0 | Midwest Regional #1 | Perrysburg BC | Gay, Todd |
| 1991 | 0 | Midwest Regional | Lake Springfield, IL | Kyle, Scott |
| 1990 | 0 | Midwest Regional | Indian Lake, OH | Scriver, Michael |
| 1989 | 0 | Midwest Regional#1 | Indian Lake, OH | Fisher, Mark |
| 1989 | 0 | Midwest Regional #2 | Clinton Lake | Wood,Paul |
| 1988 | 0 | Midwest Regional #2 | Devils Lake YC | Fries, Derrick |
| 1987 | 0 | Midwest Regional #1 | Glen Lake YC | Fries, Derrick |
| 1987 | 0 | Midwest Regional #2 | Ephraim YC | Findlay, Bob |
| 1986 | 0 | Midwest Regional | Lake Michigan, Winnetka, IL | Gay, Todd |
| 1985 | 0 | Midwest Regional | Sterling State Park, Monroe | Kyle, Scott |
| 1983 | 0 | Midwest Regional | Traverse City | Sutphen, Bruce |
| 1982 | 0 | Midwest Regional | Greater Detroit SC | Bergman, Don |
| 1981 | 0 | Midwest Regional | St. Marys BC | Draheim,Bill |
| 1980 | 0 | Midwest Regional | Cave Run Lake | Sporka,Jim |
| 1979 | 0 | Midwest Regional | Indian Lake, OH | Philbrick,Nathaniel |
| 1978 | 0 | Midwest Regional | Lake Winnebago | Gay, Todd |