2005    Kristi Trampf

2004    Melissa Staley (Top Ten Miss WI 2004) 

2003    Laura Kolar

2002    Kerri Hearden

(Non Finalist Interview Award, Spirit of Miss Wisconsin Award) 

2001    Tina Sauerhammer

(Miss Wisconsin 2003, 2nd Runner Up Miss America 2003)

(2001 - 3rd Runner Up, Marketing & Communications Award, Spirit of Miss Wisconsin Award)

2000    Lisa Arndt

1999    Kelly Marie Kujava (4th Runner Up Miss WI 1999)

1998    Tracie Lee Calkins-Delforge

1997    Jill Persick (3rd Runner Up Miss WI 1997)

1996    Paula Van Drisse

1995    Shelly Lahti (Top Ten, "Glady Award" Miss WI 1995) 

1994    Laura Voss (Miss Wisconsin 1994)

1994    Michele Lu Maye (Finished out Laura Voss' reign)

1993    No Pageant Held

1992    Darlene Swille

1991    Jill Huguet

1990    Jennifer Campbell

1989    Angela Wright

1974    Michelle Akerboom (Finished out Victoria Robbin's reign)

1974    Victoria Robbins

1973    Maryjo Steffel

1972    Karen McDiarmid

1971    Carol Ann Schmitt (Miss Wisconsin 1974)

1970    Sue Basche

1969    Janice Gonnering

1968    Nancy Gajafsky (2nd Runner up Miss Wisconsin 1968) 

1967    Terry Meeuwsen (Miss Wisconsin 1972) (Miss America 1973)

1954     Barbara Long

1951     Marlene Watermolen (1st Runner up Miss Wisconsin 1951) 

1950    Joanna Washburn

1949    Phyllis Kessler (Miss Wisconsin 1949)

1941    Dotty Duperrault

1934    Bernice Dittman

1933   Lorraine Hansen (5th Runner up Miss Wisconsin 1933)

1929   Margaret Dionne