Successful economical development of lands described earlier, slowed down the Polish – Teutonic wars from the XV century. In 1410 after the battle of Grunwald, Jagiello’s army took over Golub and Kowalewo. In 1454 year Golub and Kowalewo rejected obedience to the Teutonic order and joined the Prussian and Polish Union. During the “thirteen-year war” Kowalewo and Golub were passed on from hand to hand. Both towns and local villages were once more destroyed. Finally on the power of “The Second Peace of Thorn” the lands were included in the borders of chełmińsk's province. Both administration units were renamed into starostwa. From 1626 year Kowalewo became a base for the voivode and from 1526 there were noble local councils organized there by the chełmińsk's voivode.
In the years 1611-1625 local starostwo was rented by king’s Sigismund III Vasa sister - Anna. After death of Anna the king gave the rights to his second wife , queen Constance, later to his daughter queen Anne Catherine, and finally to queen Cecilia Renate. From the end of XVII century till the occupation in 1772 golub's starostwo was rented by following family members : Szczawińskich, Lubomirskich, Grudzińskich, Denhofów and Wesslów. In XVII century both district towns were slowly rising up from their downfall. Golub was developing successfully as a general trade center, while Kowalewo after receiving many of the kings privileges was more meaningful as a administration center.
The period of economic development was slowed down by the Swedish wars in years 1626-29, 1655-60 and 1703-18. In 1708-10 the plague disease raved on the discribed lands. During the interregnum in years 1733-35 the towns were plundered and robbed by Russian armies. During The 7 Year War (1757-63) incessantly Prussian and Russian armies crossed through Golub and Kowalewo. In 1769 for a short period the bar confederates took over Golub. In result of the fights the responsibility for taking care of the army was put on the shoulders of both towns. Besides that, the economic downfall was caused by the the egoistic politics of the nobility, which paid low taxes and it was free of custom duties. So when in year 1772 in result of The First Partition Of Poland, commissars from the Prussian government took over both towns, in Kowalewo there were only 34 houses and 296 citizens, while in Golub there were 105 houses and 658 citizens. Since than, both towns belonged to the chełmińsk's district subordinated to the Kamer and Domen department in Kwidzyń. In Golub there stood a garrison protecting borders on Drwęca. The Prussian government began new politics, importing from deep Prussia german colonists, bringing in new laws and making german the government language.
After The Third Partition Of Poland in 1795 most of the Kujawy and dobrzyń's lands were under Prussian occupation. Territory of the district lying on the south side from Drwęca was in Prussian province under the name of South Prussian poznań's department. After 1796 dobrzyń's land was subordinate to authorities in Płock, while the whole area was in the lipno's district. Napoleonic Wars had left a mark on mentioned lands. During the winter 1806-07 the French soldiery stacioned here, burdenning citiznez with numerous contributions and confiscations. After the Treaties of Tilsit the area of the present district was a part of the Duchy of Warsaw. Lands around Golub and Kowalewo were included in the Bydgoszcz's department, however dobrzyń's land was in the borders of the Płock's department. In the I half of the XIX century Golub developed quite propitiously, however there was a visible downfall of Kowalewo, which in years 1833-67 lost its town rights. In the breakthrough of XIX and XX century there were signs of economic liveliness. Communal investitions were taken in towns, there were attempts in developing the farming-food industry. In 1900 through discribed lands there was built a railroad line, conecting Bydgoszcz with Brodnica.
In result of The Treaty of Versailles form the year 1919, lands of the present district once again found themselves in the Polish nation borders. In the interwar period there were first attempts of uniting Golub with its neighbour Dobrzyń, lying in the rypin's district. This town belonged in the XIX century to the Russian Partition, it started to develope fast and in year 1939 it counted 5700 citizens, which half of it were Jewish people. At the same time in Golub there lived more than 3500 people - 90% Polish, 6% Jewish and 4% of Germans. After the German aggression on Poland between 6th and 7th September, described ladns were occupied by the Nazi army. From the very beginning the invaders began a mass extermination of the Polish population. The Germans murdered also all of the Jews who lived in Dobrzyń. During these actions most of the town buildings were destroyed. In Cieszyny near Golub, the Nazis had built a camp which was a branch camp of a concentration camp in Stuthoff. In result of the Russian armies offencive in January 1945, Germans retracted and gave a free hand to the Red Army, which without any battles had conquered 23 January 1945 Golub and Kowalewo the next day.
In a short period of time the full power in the region was taken over by a centralized communistic party-national bureaucracy. The land north from Drwęca belonged to the wąbrzesk's district, south - to the rypin's district. In 1951 the two seperate towns were nunited in a one town center. In 1956 a seperate golub-dobrzyń's district was created. Which influenced in a positive way the development of its capital - town Golub-Dobrzyń. Thanks to the rebuilding and reconstructing the castle, the town became an important touristic center. After liquidation of the districts as administration units in 1975 there was no more golub-dobrzyń's district, reactivated once more in 1999 as a result of a new administration reformation.