Incumbent Drew Dilkens holds the leading position in the Windsor, Ontario mayoral race ahead of the October 26 vote, backed by his three terms in office and recent platform emphasis on fiscal discipline, including a 2026 zero per cent property tax increase and plans for a permanent finance committee plus provincial upload of the E.C. Row Expressway. Main challenger Fred Francis, a long-serving Ward 1 councillor, trails while highlighting affordability measures, an end to strong mayor powers, and criticism of Dilkens’ record. The crowded field of 11 candidates features limited name recognition beyond these two, with minor contenders drawing negligible support. Recent campaign events, including Dilkens’ tax and oversight pledges and a minor dispute over a city hall security sweep, have reinforced trader consensus around the incumbent’s advantages in experience and provincial connections.