Incumbent Drew Dilkens holds a leading position in the October 26 Windsor mayoral race, with traders assigning him a 68% implied probability based on his 12-year record of zero or low property tax increases, infrastructure spending, and efforts to shift E.C. Row Expressway maintenance costs to the province. His main challenger, Fred Francis, sits at 22.5% as the only other candidate with prior municipal office experience; Francis emphasizes ending strong mayor powers, boosting housing affordability, and increasing council transparency. The remaining nine candidates, including Aaron Day and Kat Pasquach, register minimal odds in the crowded field. Recent campaign announcements on financial oversight and tax restraint have reinforced Dilkens’s frontrunner status ahead of advance voting.