The position of City Solicitor was established when Woburn became a city in 1889. Under the City Charter adopted at that time, the City Solicitor was appointed by the City Council. A revised City Charter was adopted in 1897, under which the Mayor is the appointing authority.
Those who have served as City Solicitor since Woburn became a city in 1889 are as follows:
| Date | Name |
| 1889-1890 | Francis P. Curran |
| 1891-1893 | Charles D. Adams |
| 1894 | Francis P. Curran |
| 1895 | Edward H. Lounsbury |
| 1896 | John P. Feeney |
| 1897 | Edward H. Lounsbury |
| 1898-1901 | Francis P. Curran |
| 1902 | Michael J. Doyle |
| 1903-1905 | George W. Norris |
| 1906-1909 | Albert F. Converse |
| 1910-1912 | Dennis L. Sullivan |
| 1913-1914 | J. Fred Maloney |
| 1915-1916 | Wilford D. Gray |
| 1917-1921 | Harold P. Johnson |
| 1922 | Philip J. Gallagher |
| 1923-1924 | James E. Henchey |
| 1924 | Wilford D. Gray |
| 1925 | William H. Henchey |
| 1925-1926 | J. Henry Rooney |
| 1926-1927 | J. Edward Begley |
| 1928-1929 | Stephen S. Bean |
| 1930 | Joseph Gorrasi |
| 1931-1933 | Stephen S. Bean |
| 1934-1937 | James H. McLaughlin |
| 1938-1949 | Joseph Gorrasi |
| 1950-1951 | James E. Henchey |
| 1952-1955 | Philip P. Dever |
| 1956-1959 | Francis P. Cullen |
| 1960 | William H. Henchey, Jr. |
| 1960 | Carl B. Everberg |
| 1961-1963 | James F. Lawton, Jr. |
| 1964-1968 | Joseph Gorrasi |
| 1968-1971 | Charles J. DiPanfilo |
| 1972 | Michael A. Gatta |
| 1972-1977 | James F. Lawton, Jr. |
| 1978-1985 | Carol J. Muller |
| 1985-2001 | Edward S. Robertson |
| 2002-2005 | Thomas W. Lawton |
| 2006-2009 | Mark R. Reich (Kopelman & Paige, P.C.) |
| 2010-2011 | John D. McElhiney |
| 2012-Current | Ellen Callahan Doucette |