[1] The Trubetsk (Troubchevsk) town was referred to in the Old East Slavic poem The Tale of Igor's Campaign where, among others, Vsevolod Svyatoslavich, the Prince of Trubetsk and of Kursk, was glorified.

In the later Middle Ages it was bordered by the Grand Duchy of Lithuania to its west and by Muscovy to its east.

In 1566 Ivan IV the Terrible took the principality during the Livonian War.

In 1654 Prince Aleksey Trubetskoy on the side of Alexis I of Russia led the southern flank of the Muscovian army from Bryansk to Ukraine.

The territory between the Dniepr and Berezyna was overrun, with Aleksey Trubetskoy taking Mstsislaw (Mstislavl) and Roslavl.