[citation needed] In the Roman period, there was a settlement called Tranatura located within the modern city municipality.

Gold, silver, lead, iron and copper were mined in the immediate vicinity and in wider surroundings of the town.

During the reign of Emperor Stefan Dušan of Serbia the mines of Kratovo were the prime source of wealth of despot Jovan Oliver.

In 1389, during his attack on Prince Lazar, Ottoman sultan Murad I stopped in Kratovo to gather information and hold a war council.

[4][better source needed] In the 15th century, Kratovo was a very important mining town, inhabited by many wealthy and educated men, such as the writer Dimitar, or Marin, son of the priest Radonja, who in 1449 donated the whole sum needed for the fresco painting of the Prohor Pčinjski monastery.

In 1484 Jovan Konik and Stefan, son of Branko, both from Kratovo, paid an amazing 16,424,000 akçe for a three-year rent of mints in Novo Brdo, Skopje and Serres.

The town of Kratovo is mentioned with the mahallahas (neighbourhoods) of Pala Gjoni with these heads of households: Jon-ko Burrnik, Pavli Jon-ko, Stepan Burrnik,; the mahalla of Radič with these heads of households: Nikolla Arbanas, Gjon domuzet, Kozma, son of Nikolla, Arbanash, Dimitri Ulko, Peja Gego, Gjergj Nikolla, Nikolla Arnaut, Bard (Bardh) Arnaut-i; the mahalla of Mahi with these heads of households: Andrenik Pavli, Gjergj Pavli, Marko Lazori, Pavli Dimitri, Petro Dimitri, Gjin Gjorgji (Gjergji), Mojsa Lazor-i; the mahalla Terzi with these heads of househoulds:Gjon terzi, Andreja Petra, Roman Petra, Simon Marko and others.

In the timar defter of 1530, the mahallah of Kodra Kuqe, meaning "red hill" in Albanian, is mentioned in Kratovo.

The inhabitants of Goldsmiths' and Minters' quarters, both Muslims and Christians, were businessmen who were famous for their investments in opening new mines such as Kučajna, Majdanpek or Kremkovica, or for leasing mints in other centers, for instance in Novo Brdo.

Seven mines were active, yielding mostly silver and copper, but a lot of ore was brought from Osogovo and mountains around Kjustendil.

[11] When the Archbishop of Antivari visited Kratovo in February 1639, he found that all 38 Catholic families were immigrants from Dibra in Albania, who could now understand the "Illyrian" (Serbian) language.

A lot of people left the town together with the Habsburg army; in early 18th century we find some of them living in Taban, the Serb suburb of Buda (today a part of Budapest).

However, mining was now done on a much smaller scale: Amu Bue in 1836 found only two furnaces working, both in bad condition, and some 5,000 – 6,000 inhabitants.

[17] After the Battle of Kumanovo, Chetnik paramilitary groups supported by the Serbian Army attacked and expelled the Albanian populations of Kratovo.

He wrote that: "Near Kratovo, General Stefanovic, having ordered hundreds of Albanians to form two rows, shot them down with machine guns.

Thereupon, the general explained: These scoundrels must be exterminated so that Austria may no longer be able to find her darlings"[19] Kratovo is known for its many reminders from the past.