Below is a list of notable people born in Kumanovo, North Macedonia, or its surroundings.
- Igor Mihajlovski (born 1973), former basketball player
- Kristijan Manević (born 1987), basketball player
- Stefan Kimevski (born 1990), handball player
- Nikola Karakolev (born 1987), basketball player
- Marko Dujković (born 1990), basketball player
- Naser Aliji (born 1993), football player
- Taulant Seferi (born 1996), football player
- Armend Alimi (born 1987), football player
- Mensur Kurtisi (born 1986), football player
- Saša Ćirić (born 1968-), former football striker
- Stole Dimitrievski (born 1993), football goalkeeper
- Vlade Lazarevski (born 1983), football player
- Nataša Mladenovska (born 1986), handball player
- Orhan Mustafi (born 1990), football striker
- Boban Nikolovski (born 1977), football player
- Redžep Redžepovski (born 1962), former boxer
- Ace Rusevski (born 1956-), former boxer
- Vujadin Stanojković (born 1962), football coach
- Oliver Spasovski (born 1976), Minister of Interior of Macedonia (2015 - 2016)
- Dragan Bogdanovski (1929–1998), émigré, activist and one of the founders of VMRO-DPMNE
- Filip Petrovski (born 1972), politician, member of Assembly of Macedonia, civil right activist, director of the National Archives of Macedonia.
- Jezdimir Bogdanski (1930-2007), president of SR Macedonia (1988–1990)
- Boris Chushkarov (1916–1982), first Director of OZNA for SR Macedonia
- Zoran Damjanovski, (born 1956), former mayor of Kumanovo
- Blage Kiprijanovski, (born 1948), mayor of Kumanovo (1993–1996)
- Slobodan Kovachevski, mayor of Kumanovo (2000–2005)
- Boris Protikj (1941–2002), mayor of Kumanovo (1996–2000)
- Saltir Putinski, mayor of Kumanovo (1951-1961)
- Teodosiy Dzhartov, mayor
- Mara Naceva, (1920–2013), Macedonian communist, participant in the World War II in Yugoslavia and a national hero
- Maksim Dimitrievski (born 1975), politician and mayor of Kumanovo
- Stanko Mladenovski (1937-), politician; Speakers of the People's Assembly
- Tode Ilich (1943–2014), mayor of Kumanovo (1984–1986)
- Trajko Loparski, former mayor of Kumanovo
- Vladimir Antonov
- Bardhi, rapper, singer
- Bodan Arsovski (born 1956), rock band member
- Ivan Babanovski (born 1941), intelligence officer and writer
- Toni Mihajlovski (born 1967), actor
- Trajko Prokopiev (1909–1979) writer
- Arif Şentürk (born 1941), folk singer and compiler
- Vanja Bulić (born 1947), journalist and TV presenter
- Venko Andonovski (born 1964), writer
- Jordan Cekov (1921–2019), partisan, journalist, writer
- Danilo Kocevski (born 1947), writer
- Slavko Dimevski (1920–1994), writer