| No. | Mayor | Took office | Left office | Prior political experience |
| – | | Francis Henry Medcalf (2nd incumbency) | 1874 | 1875 | Alderman for St. Lawrence Ward (1860)Alderman for St. David's Ward (1863, 1867–1868)Mayor (1864–1867) |
| 21 | | Angus Morrison | 1876 | 1878 | Alderman for St. James (1853–1854)Member of the Legislative Assembly of the Province of Canada for North Simcoe (1854–1863) and Niagara (1864–1867) Member of Parliament (1867–1874) |
| 22 | | James Beaty | 1879 | 1880 | Alderman for St. James's Ward (1877) |
| 23 | | William Barclay McMurrich | 1881 | 1882 | Alderman for St. Patrick's Ward (1879–1880) |
| 24 | | Arthur Radcliffe Boswell | 1883 | 1884 | Alderman for St. George's Ward (1877–1879, 1882) |
| – | | Alexander Manning (2nd incumbency) | 1885 | 1885 | Alderman for St. Lawrence Ward (1856–1858, 1867–1873)Mayor (1873) |
| 25 | | William Holmes Howland | 1886 | 1887 | President of the Toronto Board of Trade (1874–75)President of the Dominion Board of Trade (1874)President of the Manufacturers’ Association of Ontario (1877–78) |
| 26 | | Edward Frederick Clarke | 1888 | 1891 | Member of the Legislative Assembly for Toronto (1886–1894) |
| 27 | | Robert John Fleming | 1892 | 1893 | Alderman for St. David's Ward (1886–1890) |
| 28 | | Warring Kennedy | 1894 | 1895 | Alderman for St. John's Ward (1871) |
| – | | Robert John Fleming(2nd incumbency) | 1896 | 1897 (resigned August 5) | Alderman for St. David's Ward (1886–1890)Mayor (1892) |
| 29 | | John Shaw | 1897 (August 6) | 1899 | Alderman for St. Paul's Ward (1883–1895)Alderman for Ward 3 (1897) |
| 30 | | Ernest A. Macdonald | 1900 | 1900 | Alderman for St. Matthew's Ward (1886–1887, 1889–1890)Alderman for Ward 1 (1896) |
| 31 | | Oliver Aiken Howland | 1901 | 1902 | Member of the Legislative Assembly for Toronto South (1894–1898) |
| 32 | | Thomas Urquhart | 1903 | 1905 | Alderman for Ward 4 (1900–1902) |
| 33 | | Emerson Coatsworth | 1906 | 1907 | Member of Parliament for Toronto East (1891–1896)Alderman for Ward 2 (1904–1905) |
| 34 | | Joseph Oliver | 1908 | 1909 | Toronto School Board Trustee (1885)Alderman for Ward 2 (1895, 1901–1903 (also Board of Control) and 1906) |
| 35 | | George Reginald Geary | 1910 | 1912 (resigned October 21) | Toronto School Board Trustee (1904)Alderman for Ward 3 (1905–1908)Toronto Board of Control (1909) |
| 36 | | Horatio C. Hocken | 1912 | 1914 | Toronto Board of Control (1907–1909, 1911–1912) |
| 37 | | Thomas Langton Church | 1915 | 1921 | Toronto School Board Trustee (1899–1904)Alderman for Ward 2 (1905–1909)Toronto Board of Control (1910–1914) |
| 38 | | Charles A. Maguire | 1922 | 1923 | Alderman for Ward 3 (1909–1912, 1914–1917)Toronto Board of Control (1918–1921) |
| 39 | | W. W. Hiltz | 1924 | 1924 | Toronto School Board Trustee (1911–1913) Alderman for Ward 1 (1914–1920)Toronto Board of Control (1921–1923) |
| 40 | | Thomas Foster | 1925 | 1927 | Alderman for St. David Ward (1891–1892, 1894)Alderman for Ward 2 (1900–1909)Toronto Board of Control (1910, 1912–1913, 1915–1917, 1922–1924) |
| 41 | | Sam McBride | 1928 | 1929 | Alderman for Ward 3 (1905–1916)Toronto Board of Control (1917–1918, 1926, 1932–1935)Alderman for Ward 4 (1924–1925)Toronto Board of Control (1917–1918, 1926) |
| 42 | | Bert Sterling Wemp | 1930 | 1930 | Toronto School Board Trustee (1921–1922)Alderman for Ward 2 (1924–1925)Toronto Board of Control (1927–1929) |
| 43 | | William James Stewart | 1931 | 1934 | Alderman for Ward 5 (1924–1930) |
| 44 | | James Simpson | 1935 | 1935 | Toronto School Board Trustee (1905–1910)Toronto Board of Control (1914, 1930–1934) |
| – | | Sam McBride(2nd incumbency) | 1936 | 1936 (died November 10) | Alderman for Ward 3 (1905–1916)Toronto Board of Control (1917–1918, 1926, 1932–1935)Alderman for Ward 4 (1924–1925)Mayor (1928–1929) |
| 45 | | William D. Robbins | 1936 (November 18) | 1937 | Alderman for Ward 1 (1913–1917, 1923)Toronto Board of Control (1918–1919, 1925, 1928, 1930–1936) |
| 46 | | Ralph C. Day | 1938 | 1940 | Alderman for Ward 1 (1931–1934)Toronto Board of Control (1935—1937) |
| 47 | | Frederick J. Conboy | 1941 | 1944 | Alderman for Ward 6 (1935–1936)Toronto Board of Control (1937–1940) |
| 48 | | Robert Hood Saunders | 1945 | 1948 (resigned February 23) | Alderman for Ward 4 (1935–1936, 1940)Toronto Board of Control (1941–1944) |
| 49 | | Hiram E. McCallum | 1948 | 1951 | Alderman for Ward 8 (1941–1943)Toronto Board of Control (1945–1948) |