- Winner of the "What Parents Want" award presented by SchoolMatch for having the qualities most parents look for when choosing a school for their child. The SASD has been recognized every year for the last ten years.
- Sheboygan, WI was rated as the second safest metro area in the nation, by CQ Press in their publication City Crime Rankings 2009-2010. Student safety and security is a top priority for the Sheboygan Area School District.
- Grant Elementary School, Jefferson Elementary School and Washington School for Comprehensive Learning were recognized as Wisconsin Schools of Recognition for their performance during the 2009-10 school year. Jefferson Elementary School was recognized for the third year in a row. Read the press release from the Wisconsin Department of Public Instruction (DPI).
- Three SASD Schools - Farnsworth Middle School, Grant Elementary School, and Jefferson Elementary School - were recognized as New Wisconsin Promise Schools of Recognition for the 2008-2009 school year. Horace Mann and Urban middle schools have also been recognized.
- Wilson Elementary School was recognized as a 2005 Blue Ribbon School by the U.S. Department of Education based on the school’s quality of academic, co-curricular and special education programs, and staff.
- Winner of the Energy Star National Energy Pacesetter Award. Seventeen SASD Schools are energy star-rated schools. North, South, Farnsworth, Horace Mann, Jackson, Wilson, James Madison, Early Learning Center, Longfellow, Sheridan, Jefferson, Grant, Cooper, Pigeon River, Lincoln-Erdman, Grant, Washington have attained Energy Star Ratings as of April 2009.
- Grant Elementary School and Lincoln-Erdman Elementary School have received national awards for "Promising Practices" in character education.
- Washington School for Comprehensive Literacy was recognized as an Exemplary Reading Program Award winner from the Wisconsin State Reading Association and the International Reading Association. The purpose of the award is to recognize outstanding reading and language arts programs at all grade levels and to call the public's attention to outstanding programs in schools throughout North America.