Incumbent Drew Dilkens holds a clear lead in the October 26, 2026 Windsor mayoral race, with traders assigning him roughly two-thirds probability amid his bid for a fourth and final term. His positioning stems from twelve years in office, recent platform pledges to cap property tax increases at inflation, create a standing finance committee, and pursue provincial funding for infrastructure like the E.C. Row Expressway. Challenger Fred Francis, a three-term Ward 1 councillor and brother of a former mayor, trails at about one-third after launching his campaign in early September with emphasis on ending strong mayor powers, boosting transparency through monthly councillor meetings and open media briefings, and prioritizing affordability and downtown revitalization. The remaining nine candidates, including Aaron Day and Kat Pasquach, register minimal support. Recent exchanges over security sweeps at city hall and campaign spending have reinforced the two-candidate dynamic without shifting the overall consensus.