The capitol of Drevnedub, the city of Dubrovo, was founded by the warrior and holy man Mikula around 350 years ago, who built the church in the city. His descendants made a town around the church and when the Gradoslavian kniaz Ammirateus demanded tribute from them the townspeople formally stated independence from the Gradoslavian confederation of war chiefs. A young woman, Misha, living in the forrest nearby rallied the people against Ammirateus, and gathered a sizeable warband to chase away Ammirateus and his men. When Gradoslavl was attacked by Frakians, Drevnedub came to their aid, led by the warrior Bereslav, who was elected warleader by the Drevnedubians. However, when the Black Magi established themselves in Kardomir, Gradoslavl did not come to Drevnedubs aid, leading to quite some biterness. This was eventually laid to rest through a marriage between Kniaz Dobroslav of Gradoslavl and Cvetana, the daughter of the Drevnedubian kniaz. Old slights were for a time forgotten to forge an alliance against the black magic using Black Magi of Kardomir. The province came under feudal allegiance to the kniaz of Gradoslavl and Kardomir when the kniaz of Drevnedub died. Kniaz Dobroslav, who by that time had titled himself tzar, had been seen as such a great leader that he was then elected kniaz of Drevendub. When he died, tsaritsa Cvetana returned to Drevnedub and was elected kniaginia of Drevnedub, making her head of both provinces. She was succeeded by her youngest son, who was elected kniaz of Drevnedub with the tzar as his feudal lord. The province retained its own laws, the election of their kniaz by the commoners, their lawmen called the Elders that have the right and duty to recite and interpret the laws, and the right for commoners to arm themselves. Drevnedub continued the tradition of having bogatirs as the retinue of the kniaz that was abandoned by Triman in favour of knights sworn only to the tzar. As part of Triman, Drevnedub worked closely with the church when it came to laws for the kingdom. However, there were many disagreements between Trimans church of Svarog and Drevnedubs church of Svarog on religious issues, making them abandon each during the reign of tsaritsa Miloluba. The Elders of Drevnedub refused further interaction with the rest of the kingdom. Beggar knights were however welcome in Drevnedub, as they were part of the bogatir order. They would often take the role of unofficial negotiators between the church of Trimand and the Elders of Drevnedub.
With Ledoslavl emerging at the borders of Drevnedub, the church of Drevnedub was attacked anew. The people inhabiting the border between Drevnedub and Ledoslavl had mostly followed practices of Drevnedub. However, the new rulers wanted to bring them to follow the practices of the rest of the kingdom, and branded those refusing as heretics. The church of Triman sided against Drevnedub in this matter, and Drevnedub withdrew even more.
Ledoslavl saw this as weakness, and tried to take Drevnedub territories. This was however met with strong military resistance, and Ledoslavl had to withdraw. To this day there is no peace between Ledoslavl and Drevnedub, with both sides expecting an attack from the other.
When the tzar Vsevolod the Cruel started his campaign against the church of Triman, the province had been neutral, refusing to aid either side. At this time Frakian troops marched through Ledoslavl and attacked Drevnedub. They were led by the magister of the Angel Knights who saw the old practices of Drevnedub as heretical. The Frakians burned and sacked Vailano through the use of dark magic and killed the kniaz in battle. They then marched on Dubrovo. The crimes of the magister of the Angel Knights in Vostokograd were so gruesome that an angel of Svarog was sent to raise the dead and march them to fight in the siege of Dubrovo. With most of the militia of Drevnedub fallen in battle, and no kniaz to lead them, Dubrovo had a poor chance to stand. However, old Bereslav, the former kniaz, appeared before the council of elders and was tasked with leading the militia. With the dead breaking the siege and Bereslav holding the walls of Dubrovo, the besieging Angel Knights were defeated. In the battle it was also revealed that the magister of the Angel Knights was himself in pact with the Black Serpent, channeling the power of a demon through himself to gain more power. After this battle, and with the churches being plundered by the tsars soldiers, the Elders decided to intervene. A new kniaz was named and tasked with marching the irregular army of Drevnedub and the remaining bogatir against Vsevolod the Cruel, forcing the Tzars army to retreat to central Triman. There 3 copper knights met the Tzars army and made the Tzar sign a peace treaty between the church and state. The Tzar reluctantly signed, however he still saw the kniaz of Drevnedub as traitor, and declared him cut off from the line of inheritance to the throne.