Incumbent Drew Dilkens holds a narrow lead in trader consensus for the Windsor mayoral race ahead of the October 26 vote, reflecting his established record on major infrastructure projects and recent platform releases on downtown revitalization and community safety. Challenger Fred Francis trails as the main alternative, buoyed by targeted proposals to expand affordable housing through tax incentives, fee waivers, and density reforms that have drawn attention in the final weeks. Multiple debates have highlighted contrasts on policing resources, transit restoration, and homelessness strategies, while a crowded field of lesser-known candidates fragments remaining support. Advance voting is underway, and the race remains closely contested with limited polling data available to shift implied probabilities further before election day.