Harold Gilleshammer (born April 8, 1942) is a Canadian judge and former politician in Manitoba, Canada. He was a member of the Manitoba legislature from 1988 to 2003, He obtained a Bachelor of Arts in History, Political Science and English from the University of Manitoba and a Bachelor of Education from Brandon University. He subsequently worked as a teacher. The Progressive Conservatives formed a minority government after the election, although Gilleshammer was not initially appointed to cabinet.
Provincial support for the Liberal Party declined in 1990, and Gilleshammer defeated Drebit by over 2000 votes in that year's provincial election, in a rematch between the two candidates.