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This principality was split out of Moscow land about 1241 according to the testament of Ivan I Danilovich. He gave it to his son Andreei. At that time it consisted of a collection of 22 villages and didn't have a capital town. Serpukhov fortress town was built on the Oka River by Vladimir Andryeyevich in 1374 as part of the main defense line for Muscovy. He expanded the boundaries of the principality in the basins of the Nara and Protva rivers. About 1378 Vladimir Andryeyevich received from Dmitrii Donskoi Borovsk town with its volosts (now in Kaluga oblast). Vladimir also served at court and on campaign with Dmitrii. He was especially famous for his conduct at Kulikovo Battle in 1380.
I n1410 Vladimir divided his otchina between his sons into udels at Maloyaroslavich, Borovsk, Radonyezh, Pyeryemishl and Serpukhov itself. Serpukhov went to his son Ivan. The other four, small udels were only slightly connected with Serpukhov itself. Ivan Vladimirovich Serpukhovski held the now small principality with only 7 suburbs and 7 volosts.
VAsiliii Yaroslavich was a loyal supporter of Vasilii II against Dmitrii Shemyaka. Vasilii gave him Dmitrov, Sukhodol and other towns a part of which he returned later to the grand prince in exchange for other volosts. But he was able again to unite into his hands all the territories held by Vladimir Andryeyevich, creating again a united Serpukhov-Borov principality. Vasilii Yaroslavich in 1456 with his sons was exiled to Uglich and then to Vologda where he died in 1483. His second wife fled to Lithuania and Serpukhov principality was united into Muscovy. In 1462 a group of 'deti boyarski' atteempted to free Vasilii Yaroslavich but were caught and executed. His son, Ivan, died in Lithuania and Ivan's children became servitors of Lithuania and Poland. Other sons of Vasilii Yaroslavich, Andrei and Vasilii died apparently in exile. According to Vasilii II testament Serpukhov was given to his son Yuri, and Borovsk to Ivan III. At the death of Yurii Vasili'yevich in 1472 the grand prince funally reunited Serpukhov to Moscow.


- 1341 - 1352 - Andrei Ivanovich
- 1352 - 1358 - Ivan Andryeyevich
- 1358 - 1410- Vladimir Andryeyevich Khrabrii
- Ivan Vladimirovich
- 1456 - Vasilii Yaroslavich
- 1472 - Yuri Vasil'yevich


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