The history of Kutno is many centuries old and contains both periods of prosperity and decline. The city enjoyed long years of success under the reigns of diligent and enlightened owners; it also struggled with crises following turbulent history of Poland and the disintegration of feudal structures. The town of Kutno was originated in a place which had often been settled in ancient times. Recent archeological research carried out in the area of Kutno have led to some interesting discoveries of new settlements of East-Pomeranian culture, most interesting of them being: a box grave from the village of Kręcieszki, Bedlno community, dating back to the late Hallstattan period (550-400 BC) and containing as many as 42 urns, and a pit grave, unusual for that culture, from Florek, Kutno community. The latter comes from the early La Tene (400 BC - early AD).

The market privilege bestowed by prince Siemowit IV of Płock in 1386 marks the beginning of Kutno's municipal character. The privilege was given to Andrzej of Radzikowo for his devoted duty for the prince during his endeavors to attain the Polish crown. That act freed residents of Kutno from any fees, levies and burdens saved two grosze per feud. Besides, it released them from the jurisdiction of land courts so residents were liable to the prince and landowners only. Finally, the prince allowed them to trade on Mondays and have fairs on the Feast of St. Lawrence's. The market privilege was crucial for further development of Kutno which had already been a well-organized place since there was a parish church there. The origins of Kutno parish might have begun even in the first half of the 13th century. Two facts seem to testify to that date: the vast parish contained 14 villages and the church patron - St. Lawrence whose cult became popular in Poland at the turn of 13th century. The construction of a stone church in the early 15th century also shows the importance of Kutno as a religious centre. The new church is a result of Andrzej of Radzikowo's patronage.

In the case of Kutno the foundation charter based on German Law is unknown, however, the latest research concerning the town's origins points to the market privilege as the proper document because such deeds used to be equal to foundation of a town in the region of Mazowsze. Therefore, we may suppose that also about the year 1386 a municipal self-government was formed. Still, the first unambiguous mention of Kutno as a city comes from a document issued as late as in 1444. Similarly, from the 1430's residents of Kutno were called "oppidiani" (burghers) or "providi" and both names were used in reference to townspeople. The oldest town's seal of Kutno comes from that earliest period and depicts two wild boars in an antithetic arrangement with a cyperaceous herb in between. There is an inscription written in Gothic: "sigillum civitatis kuthnensis" going round the artwork.

Andrzej of Radzikowo was the progenitor of the Kucieński family who had owned the city since 1689. Mikołaj Kucieński (ca. 1430 - 1493), a voivode of Łęczyca and general starost of Wielkopolska originated the greatness of his family. He also belonged to the closest circle of king Kazimierz Jagiellończyk's court. In 1462, after the death of Władysław II, the prince of Mazowsze, he made a clear-cut offer to submit his castle at Gostynin to the king thus incorporating the land of Gostynin and his property directly to the crown of Poland.