The Mayor of Annapolis is the chief political figure in the city of Annapolis, which is the capital city of Maryland. The mayor is elected to a four-year term.

• 1708–1720 Amos Garrett
• 1720–1721 Thomas Larkin
• 1721–1722 Benjamin Tasker
• 1722–1726 Vachel Denton
• 1726–1727 Benjamin Tasker
• 1727–1745 Vachel Denton
• 1745–1746 Robert Gordon
• 1746–1747 Michael MacNamara
• 1747–1748 Benjamin Tasker
• 1748–1749 John Ross
• 1749–1750 John Bullen
• 1750–1753 Benjamin Tasker
• 1753–1754 Michael MacNamara
• 1754–1755 Benjamin Tasker, Jr.
• 1755–1756 John Brice, Jr.
• 1756–1757 Benjamin Tasker
• 1757–1758 John Bullen
• 1758–1759 John Ross
• 1759–1760 Dr George H. Steuart
• 1760–1761 Michael MacNamara (MacNamara left Annapolis for England in April, 1761)
• 1761–1762 Stephen Bordley (elected to serve out the rest of MacNamara's term)
• 1762–1763 John Brice, Jr.
• 1763–1764 Dr George H. Steuart
• 1764–1765 Daniel Dulany
• 1765–1766 John Ross
• 1766–1767 Walter Dulany
• 1767–1768 Upton Scott
• 1771–1772 Thomas Jennings
• 1773–1780 Allen Quynn
• 1780–1781 John Brice III
• 1781–1782 John Bullen
• 1782–1783 James Brice
• 1783–1784 Jeremiah Townly Chase
• 1784–1785 Nicholas Carroll
• 1785–1786 Robert Couden
• 1786–1787 Allen Quynn
• 1787–1788 James Brice
• 1788–1789 John Bullen
• 1789–1790 Nicholas Carroll
• 1790–1791 Robert Couden
• 1791–1792 Allen Quynn
• 1792–1793 John Bullen
• 1793–1794 James Williams
• 1794–1795 William Pinkney
• 1795–1796 Allen Quynn
• 1796–1797 John Bullen
• 1797–1798 Philip Barton Key
• 1798–1799 Nicholas Carroll
• 1799–1800 John Davidson
• 1800–1801 James Williams
• 1801–1802 Allen Quynn
• 1802–1803 Samuel Ridout
• 1803–1804 John Johnson
• 1804–1805 James Williams
• 1805–1806 Samuel Ridout
• 1806–1807 Burton Whetcroft
• 1807–1808 John Kilty
• 1808–1809 Burton Whetcroft
• 1809–1810 John Johnson
• 1810–1811 Nicholas Brewer
• 1811–1812 Gideon White
• 1812–1813 Nicholas Brewer
• 1813–1814 John Randall
• 1814–1815 Nicholas Brewer
• 1815–1816 John Randall
• 1816–1817 Nicholas Brewer
• 1817–1818 John Randall
• 1818–1819 Nicholas Brewer
• 1819–1823 Lewis Duvall
• 1823–1825 James Boyle
• 1825–1828 Richard Harwood of Thomas
• 1828–1837 Dr. Dennis Claude
• 1837–1840 John Miller
• 1840–1843 Alexander Contee Magruder
• 1843–1845 Richard Swann
• 1845–1846 William Bryan
• 1846–1848 Richard Swann
• 1848–1849 Richard Goodwin
• 1849–1851 Dr. Abram Claude
• 1851–1852 Brice Worthington
• 1852–1853 Richard Goodwin
• 1853–1854 Dr. Dennis Claude
• 1854–1855 Dr. Abram Claude
• 1855–1856 Nicholas Brewer, III
• 1856–1858 Richard Swann
• 1858–1859 Joseph Brown
• 1859–1860 William Harwood
• 1860–1862 John Magruder
• 1862–1863 Wesley White
• 1863–1864 John Magruder
• 1864–1865 Solomon Phillips
• 1865–1866 Richard Goodwin
• 1866–1867 Richard Swann
• 1867–1869 Dr. Abram Claude
• 1869–1870 Augustus Gassaway
• 1870–1871 John Hyde (D)
• 1871–1875 James Munroe
• 1875–1877 Arthur Wells
• 1877–1879 James Brown
• 1879–1883 Thomas Martin
• 1883–1889 Dr. Abram Claude
• 1889–1893 James Brown
• 1893–1897 John Thomas
• 1897–1899 Dr. Richard Green
• 1899 Nevett Steele (Steele was elected mayor February 13, 1899, to fill the unexpired term of Green, who had died the month before. Steele served until the election of Seidewitz in July.)
• 1899–1901 Edwin Seidewitz
• 1901–1903 Charles Dubois (R)
• 1903–1905 Samuel Jones
• 1905–1907 John Douw
• 1907–1909 Gordon Claude (D)
• 1909–1919 James F. Strange (D)
• 1919–1921 John Levy (D)
• 1921–1923 Samuel Jones
• 1923–1925 Charles Smith
• 1925–1927 Allen Bowie Howard (D)
• 1927–1929 Charles Smith
• 1929–1935 Walter Quenstedt (R)
• 1935–1939 Louis Phipps (D)
• 1939–1941 George Haley (acting mayor, Jan. 17, 1939 to July 21, 1941)
• 1941–1949 William McCready (D)
• 1949–1952 Roscoe Rowe (R)
• 1952 Robert Campbell, Sr. (acting mayor following Rowe's death, nine months of 1952)
• 1952–1961 Arthur Ellington (D, acting mayor, Jan. 15 to July 20, 1953)
• 1961–1965 Joseph Griscom, Sr. (R)
• 1965–1973 Roger Moyer (D)
• 1973 Noah Hillman (D, Served June 2 to 11; Moyer resigned 10 days before the end of his term as a way to honor Hillman, a long-time City Councilmen).
• 1973 – March 9, 1981 John Apostol (R, resigned March 3, 1981)
• March 9, 1981 – April 12, 1981 Gustav Akerland (R, Alderman and acting mayor following Apostol's resignation; died April 15, 1981).^[1]
• April 12, 1981 – June 7, 1981 John Thomas Chambers, Jr. (R, Alderman and acting mayor following Akerland's suicide; Annapolis’ first African-American Mayor).
• 1981–1985 Richard Lazer Hillman (R)
• 1985–1989 Dennis Callahan (D)
• 1989– December 1, 1997 Alfred Hopkins (D)
• December 1, 1997 – December 3, 2001 Dean Johnson (R)
• December 3, 2001 – December 7, 2009 Ellen Moyer (D)
• December 7, 2009 – December 2, 2013 Joshua Cohen (D)
• December 2, 2013 – December 4, 2017 Mike Pantelides (R)
• December 4, 2017 – Present Gavin Buckley (D)

• "Archives of Maryland Historical List Annapolis Mayors, 1708--". msa.maryland.gov. Maryland State Archives. December 4, 2017. Retrieved April 13, 2020.
• "Annapolis, Maryland - Government". Maryland Manual On-Line. Maryland State Archives. April 7, 2020. Retrieved April 13, 2020.
• "Annapolis Mayors, Maryland - Government". Maryland Manual On-Line. Maryland State Archives. December 4, 2017. Retrieved April 13, 2020.