Incumbent Drew Dilkens, mayor since 2014, holds the leading position in the October 26, 2026 Windsor mayoral contest following his late nomination filing on the August 21 deadline. He frames his fourth and final term around continuity for major projects such as Sandwich South development and managing trade pressures, while noting extensive prior use of strong-mayor authority. Main challenger Fred Francis, a sitting Ward 1 councillor, campaigns on change, emphasizing tax restraint, debt reduction, affordability, safety, and downtown revitalization. The 11-candidate field, with several low-profile entrants, fragments opposition support. Traders assign Dilkens the highest probability based on incumbency patterns in Ontario municipal races, while Francis trails and minor candidates register minimal implied odds ahead of the vote.