The Best Upset ESPY Award was conferred once each in 2004 and 2005 annually from 2007 until 2017 and again in 2019 to the team in a regular season or playoff game or series contested professionally under the auspices of one of the four major sports leagues in the United States and Canada or collegiately under the auspices of the National Collegiate Athletic Association adjudged to have completed the best, most significant, or most impressive upset in a given calendar year. There was no award presented in 2018, 2020 or 2021; however, an award was presented in 2019.