This is a list of mayors of Kumanovo, North Macedonia.[1]
| width=190 | Name (Born–Died) | Portrait | Elected | Term of office | Political affiliation | ||
|---|---|---|---|---|---|---|---|
| Ottoman Empire (Kumanovo Kaza 1867-1912 Kaymakam) Kingdom of Yugoslavia (1918 onward) | |||||||
| 1 | Kjira Andjelkovic | 1918 | 1918 | 1920 | |||
| 2 | Kosta Daljev[2] | 1920 | 1920 | 1921 | Komunist Party | ||
| 3 | Toma Gligorijevic first term | 1922 | 1922 | 1924 | |||
| 4 | Gjorgje Mladenovikj | 1924 | 1924 | 1926 | |||
| 5 | Toma Gligorijevic second term | 1926 | 1926 | 1929 | |||
| 6 | Kjira Manevich first term [3] | 1929 | 1929 | 1935 | |||
| 7 | Toma Gligorijevic third term | 1935 | 1935 | 1936 | |||
| 8 | Kjira Manevich second term | 1936 | 1936 | 1936 | |||
| 9 | Nikola Stojanovski | 1936 | 1936 | 1937 | |||
| 10 | Dragomir Vukadinovikj | 1937 | 1937 | 1938 | |||
| 11 | Trajko Loparski | 1939 | 1939 | 1940 | Jugoslovenska Radikalna Zaednica[4] | ||
| 12 | Kjira Manevich third term | 1940 | 1940 | 1941 | |||
| Bulgaria (1941-1945) | |||||||
| 1 | Teodosiy Dzhartov | 1941 | 1941 | 1941 | Bulgarian Action Committees | ||
| 1 | Milan Gotsev[5] | 1941 | 1944 | 1944 | Bulgarian Action Committees | ||
| 2 | Josif Andonov[6] | 1944 | 1944 | 1944 | Bulgarian Action Committees | ||
| Socialist Federative Republic of Yugoslavia (1945-1990) | |||||||
| 1 | Nikola Peshev[7] | 1945 | 1945 | ? | Communist Party of Yugoslavia | ||
| 2 | Saltir Putinski[8] | 1951 | 1951 | 1961 | Communist Party of Yugoslavia | ||
| 3 | Jezdimir Bogdanski[9] (1930–2007) | 1963 | 1963 | 1969 | Communist Party of Yugoslavia | ||
| 4 | Blashko Janevski[10] (1930–2007) | 1972 | 1972 | 1972 | Communist Party of Yugoslavia | ||
| 5 | Metodi Petrovski[11] | 1974 | 1974 | 1978 | Communist Party of Yugoslavia | ||
| 6 | Metodi Petrovski[12] | 1978 | 1978 | 1982 | Communist Party of Yugoslavia | ||
| 7 | Momchilo Jovanovski (August 1, 1931-2016) [13] | 1982 | 1982[14] | 1986[15] | Communist Party of Yugoslavia | ||
| 8 | Tode Ilich[16] (1943-2014) | 1984 | 1984 | 1986 | Communist Party of Yugoslavia | ||
| R Macedonia (1991 onward) | |||||||
| 1 |  Blage Kiprijanovski(1948-) | 1991 | 1991 | 1996 | Social Democratic Union of Macedonia | ||
| 2 | Boris Protikj (1941-2006) | 1996 | 1996 | 2000 | Social Democratic Union of Macedonia | ||
| 3 | Slobodan Kovachevski | 2000 | 2000 | 2005 | Social Democratic Union of Macedonia | ||
| 4 | Zoran Damjanovski (1956-) | 2005 | 2005 | 2009 | Social Democratic Union of Macedonia | ||
| 5 | Zoran Damjanovski second term (1956-) | 2009 | 2009 | 2013 | Social Democratic Union of Macedonia | ||
| 6 | Zoran Damjanovski third term (1956-) | 2013 | 2013 | 2017 | Social Democratic Union of Macedonia | ||
| 7 | Maksim Dimitrievski (1975-) | 2017 | 2017 | 2021 | Social Democratic Union of Macedonia | ||
| 8 | Maksim Dimitrievski (1975-) | 2021 | 2021 | incumbent | Independent | ||