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

• Velika Begovica (fl. 1876–78), rebel leader
• Hristijan Todorovski Karpoš (1921–1944), communist partisan during the Second World War
• Goran Georgievski (1969–2005), member of Lions (fl. 2001-04)
• Ismet Jashari (1967–1998 †), commander (Kumanova) Kosovo Liberation Army
• Boban Trajkovski (1973–2001 †), member of Wolves
• Jovan Dovezenski (1873–1935), commander (vojvoda)
• Pavle Mladenović - Čiča Pavle (-1905), commander (vojvoda)

• Timotej of Debar and Kichevo (born 1951), current Mitropolitian of Diciose of Debar and Kuchevo (fl. 1995–present)
• Hilarion of Bregalica (1973-), current Mitropolitian of Diciose of Bregalnica (fl. 2006–present)
• Hadži-Zaharija (1760–1830) Metropolitan of Raška and Prizren (fl. 1819–30)
• Denko Krstić (1824–1882), influential merchant, born in Mlado Nagoričane
• Dimitrije Mladenović (1794–1890), Orthodox archpriest, born in Proevce (fl. 1833-90)

• Valentin Ilievski general director of the Messer Group for BiH
• Denko Krstić

• Romeo Zhivikj - Roki, (1962–2004) Crime Boss (fl. 1980-2004)
• Bajrush Sejdiu, (born 1968) leader of Bajrush gang (fl. 1990-2008)
• Nezim Allii, leader of Nezim gang (fl. 2004–2014)