- 1956-57 was the first year Wisconsin participated in the CCSSO Teacher of the Year program and identified a state Teacher of the Year. Merle N. Pickett from Washington Junior High School in the Manitowoc School District was considered a National Teacher of the Year Finalist (in a field of 10 teachers, where 9 were finalists and the Missouri Teacher of the Year was named the National TOY).
- 1982-83 is the first year there is a record of there being 4 Wisconsin Teachers of the Year—one each in Elementary, Middle/Junior High, High School, and Special Services.
- Wisconsin has had one teacher selected as a state Teacher of the Year twice: Edward Mueller, of Horace Mann Junior High School in Neenah, was first identified as the state representative in the 1967-68 school year (1968 WI Teacher of the Year) and then again in the 1983-84 school year—16 years later!
- In 1990, then US Senator Herb Kohl founded the Herb Kohl Educational Foundation, whose mission includes improving education, economic opportunity and quality of life for the people of Milwaukee and Wisconsin. The Kohl Foundation awards Teacher Fellowships to 86 public school and 14 private school teachers annually.
- Educators are chosen for the Herb Kohl Teacher Fellowship for their ability to inspire a love of learning in their students and ability to motivate others, and for their leadership and service within and outside the classroom. By 1993, four Wisconsin Teachers of the Year were being drawn from the pool of 86 Kohl Fellows each year.
- In 2003, the Herb Kohl Educational Foundation began awarding additional funds to support the co-sponsoring the Teacher of the Year program, granting additional awards to the four TOYs and an additional award to the one representing Wisconsin at the national level.
- 2019 saw the diversity of the state of Wisconsin better represented, with Waqnahwew Benjamin Grignon selected as Wisconsin's first every Teacher of the Year from one of the eleven federally recognized tribal nations of Wisconsin (Menominee), and Sarahí Monterrey selected to serve as the Wisconsin representative to the National Teacher of the Year program, the first Latina from Wisconsin to serve in this capacity.
- Between 1956 and 2019, Wisconsin's representative for the Council of Chief State School Officers (CCSSO) National Teacher of the Year Program has included:
- 18 Elementary School Teachers of the Year
- 16 Middle School Teachers of the Year
- 21 High School Teachers of the Year
- 3 Special Services Teachers of the Year
- 2 teachers whose role was unknown (in 1962-63, and again in 1968-69)
Wisconsin’s National Teacher of the Year Finalists
Wisconsin has had 6 Finalists for the National Teacher of the Year, with one being named National Teacher of the Year:
1957: Merle N. Pickett, Washington Jr. High School (Manitowoc)
1961: Helen "Missy" Adams, Cumberland Elementary School, National Teacher of the Year
1964: William E. Dunwiddle, Neenah High School
1966: Syble Hopp, Donovan School for Retarded Children (Green Bay)
1967: Paul D. Plantico, Green Bay West High School
2017: Chris Gleason, Patrick Marsh Middle School (Sun Prairie Area School District)
Wisconsin’s National Teacher of the Year: Helen “Missy” Adams
Kindergarten teacher Helen “Missy” Adams, from Cumberland Elementary School in the Cumberland School District, was the 1961 National Teacher of the Year, and received her award from President Kennedy. Her story was featured in the May 23, 1961 issue of “Look” magazine, where she called for a focus on early childhood mental health supports nearly half a century before the concept was brought to the forefront of comprehensive educational practices. Also a survivor of polio, she retired after 55 years in the classroom.