In 1912, during the First Balkan War, Serbian forces won a decisive victory over the Ottomans north of the town.

The two-day Battle of Kumanovo ended Ottoman authority in Vardar Macedonia which contributed to the region's integration into Serbia, and consequently, into Yugoslavia.

During World War II the communist resistance in Vardar Macedonia began in Kumanovo on 11 October 1941.

The town's metal-processing, tobacco, agriculture, footwear and textile industries made it an economic, trading and cultural center during the time of SFR Yugoslavia.

The name comes from the merchants from the town of Veles, who passed through the neighbourhood to sell their products by the rivers Vardar and Pchinja, and the Konjarinja villages Studena, Bara and Krasta.

The main street, which today is named Narodna Revolucija, was their shortest way to the center of the city.

MB Hristijan Todorovski Karposh is the second base in Kumanovo, it was also established by the JNA and was inherited by the ARM.

These are, for the most part, found in Serbian charters: In this time, the Kumanovo region (old Žegligovo) received its geographical location and certain settlement picture.

It included the old župe (counties) of Žegligovo and Preševo (modern Kumanovo region with Sredorek and Kozjačija).

The mosque in the downtown is beautiful, there are tekke, madrassa, hammam, a number of shops and water mills; and the climate is pleasant and agreeable.

Karposh's Rebellion quickly spread, resulting in the liberation of Kratovo, Kriva Palanka, Kumanovo, Kačanik and other towns.

Then, together with the Austrian army led by Emperor Leopold I, the local Christian population fought to liberate Skopje and Štip.

The Austrian army was forced to withdraw and the reinforced Ottomans attacked the rebels, taking Kriva Palanka, the rebel stronghold, and then attacked Kumanovo and its newly constructed fortress, where they captured Karposh and put him to death on the Stone Bridge across the Vardar.

The two-day Battle of Kumanovo ended Ottoman authority in Vardar Macedonia and contributed for region's integration into Serbia, and consequently, into Yugoslavia.

The armed conflict in Kumanovo mainly resulted in a division of the educational system along ethnic lines.

[34] After the Second World War the town's metal-processing, tobacco, agriculture, footwear and textile industries have made it an economic, trading and cultural center during the time of SFR Yugoslavia.

Section of the Pan-European Corridor X was put into use in 2010 connecting Kumanovo to the border crossing Tabanovce.

Other landmarks are: buildings: and The oldest folklore assemble in North Macedonia, KUD "Panče Pešev" is placed in Kumanovo.

KF Goblen has played in the Macedonian Second Football League and FK Karpoš 93 in the OFS Kumanovo First Division.

Macedonian National Football Team played friendly match with Egypt in Kumanovo on 29 September 1998.

The game took place at Gradski Stadium Kumanovo and the scorers for Macedonian team were Srgjan Zaharievski and Dževdet Šainovski.

Romania Honorary Consulate[37] Kumanovo is twinned with:[38] Ти помени већим делом налазе се у даровним повељама српских давалаца: краља Милутина, цара Сте- фана Душана, севастократа Дејана, Јевдокије Дејановић2', Дејано- вих синова – браће деспота Драгаша и "господина" Константина.

Као што се зна, тада је ова област – старо Жеглигово до- била учвршћен географски положај и одрећену насеобинску сликупрема повељи манастиру богоро- дичимог ваведења у Архиљевици,50 држао као своју баштину пространу област иеточно од Скопске Црне Горе.

Она је обухватала старе жупе Прешево и Жеглигово (данас кумановски крај са Средореком, Козјачијом