It is known since XI century. In XII century it became the centre of Starodubs'ke principality. Since XIV century it was part of the Great Lithuanian principality. In 1503-1618 it was under the power of Moskow state, later it belonged to Poland.
In 1620 it has received the Magdeburg Right.
Since 1648 it was the centre of Starodub regiment.
On the princes' seals of the middle of the XII century there was an oak. The old symbol of the city was confirmed as an emblem by Sigizmund III. The seal of the city had the picture of St.George.
Untill 1919 it belonged to Chernihivs'ka province.