Weyburn was founded in 1899 and achieved city status in 1913. Below is a historical list of mayors from incorporation to present.
| PAST MAYORS | |
| ?? | Overseer Alex Mitchell |
| 1902 | Overseer P.E. Metheral |
| 1903 | Overseer Alf Wood |
| 1903 | Mayor T. Blacklock |
| 1904 | Mayor R.M. Mitchell |
| 1905 | Mayor W.M. Kellock |
| 1906 | Mayor N.D. McKinnon |
| 1907 | Mayor R.M. Mitchell |
| 1908 | Mayor W. Monaghan |
| 1909 | Mayor J. Russell Fox |
| 1910 | Mayor Rick Smith |
| 1911-1914 | Mayor J. McTaggart |
| 1915-1917 | Mayor Dr. G.M. Bowman |
| 1918-1919 | Mayor F.B. Moffat |
| 1920 | Mayor Dr. G.W Bowman |
| 1921-1924 | Mayor Jos. Mergens |
| 1925 | Mayor Thompson McLelland |
| 1926-1929 | Mayor Dr. J.K. Brimacombe |
| 1930-1931 | Mayor David Aitken |
| 1932-1933 | Mayor Dr. J.K. Brimacombe |
| 1934-1938 | Mayor W.H. Duncan |
| 1939-1941 | Mayor Dr. J.K. Brimacombe |
| 1924-1945 | Mayor Jos. H. Warren |
| 1946 | Mayor H.M. Harvey |
| 1947 | Mayor Jos. W. Warren |
| 1948 | Mayor R.H. Rick Smith & Mayor J.H. Warren |
| 1949-1951 | Mayor R.H. Rick Smith |
| 1952-1953 | Mayor Dr. F.C. Eaglesham |
| 1954-1959 | Mayor J.H. Staveley |
| 1960-1962 | Mayor Albert J. Onstad |
| 1963-1966 | Mayor T.G. Laing |
| 1967-1976 | Mayor T.A. Tom Hart |
| 1977-1982 | Mayor M. Isabelle Butters |
| 1983-1985 | Mayor Gordon Miles |
| 1986-1988 | Mayor W.A. Shields |
| 1989-1991 | Mayor Ronald E. Barber |
| 1992-1997 | Mayor James A. Brown |
| 1998-2006 | Mayor Donald E. Schlosser |
| 2007-2016 | Mayor Debra Button |
| 2016-2024 | Mayor Marcel Roy |
| 2024-Present | Mayor Jeff Richards |