Vladimir Andreyevich the Bold (Russian: Владимир Андреевич Храбрый) (July 15, 1353 – 1410) was the most famous prince of Serpukhov. His moniker alludes to his many military exploits committed in the wars waged by his cousin, Dmitri Donskoi of Moscow.
A grandson of Ivan Kalita, Vladimir inherited Serpukhov, Borovsk, and a third part of Moscow from his brother at the age of 5. As his cousin Dmitry of Moscow was also a child, both princes had to be tutored by the Metropolitan Alexis who arranged a treaty stipulating Vladimir's loyalty to his Muscovite cousin.
Pursuant to the treaty, Vladimir helped Dmitry to fight Tver (1375), Ryazan (1385), the Livonian Knights (1379), and the Republic of Novgorod (1392). Although he married a daughter of Algirdas of Lithuania in 1371, Vladimir still loyally supported Dmitry in his struggle against the Lithuanians.
In 1374, anxious to defend his capital, Vladimir built the first oaken kremlin in Serpukhov. In 1377, Vladimir sacked the Severian towns of Trubchevsk and Starodub. In the great Battle of Kulikovo (1380) Vladimir commanded cavalry which decided the Russian victory. When Tokhtamysh invaded Russia two years later, Vladimir defeated his force near Volokolamsk.