It was founded in the late 14th century by Vladimir the Bold and named Yaroslavets after his son Yaroslav.[9] In 1485, the town was annexed by the Grand Duchy of Moscow and renamed Maloyaroslavets to distinguish it from Yaroslavl.[citation needed] During the French invasion of Russia, the Battle of Maloyaroslavets took place near this town on October 12 (24) of 1812. The battle was commemorated by a roomy cathedral built at the Black Island (Chyornoostrovsky) Convent of Maloyaroslavets by 1843.
A number of fierce battles were also fought near Maloyaroslavets during the Battle of Moscow in 1941–1942. The town was under German occupation from 18 October 1941 until 2 January 1942. It was liberated by troops of the Western Front of the Red Army.[10]
Законодательное Собрание Калужской области. Закон №7-ОЗ от 28 декабря 2004 г. «Об установлении границ муниципальных образований, расположенных на территории административно-территориальных единиц "Бабынинский район", "Боровский район", "Дзержинский район", "Жиздринский район", "Жуковский район", "Износковский район", "Козельский район", "Малоярославецкий район", "Мосальский район", "Ферзиковский район", "Хвастовичский район", "город Калуга", "город Обнинск", и наделении их статусом городского поселения, сельского поселения, городского округа, муниципального района», в ред. Закона №620-ОЗ от 29 сентября 2014 г. «О внесении изменений в Закон Калужской области "Об установлении границ муниципальных образований, расположенных на территории административно-территориальных единиц "Бабынинский район", "Боровский район", "Дзержинский район", "Жиздринский район", "Жуковский район", "Износковский район", "Козельский район", "Малоярославецкий район", "Мосальский район", "Ферзиковский район", "Хвастовичский район", "город Калуга", "город Обнинск", и наделении их статусом городского поселения, сельского поселения, городского округа, муниципального района"». Вступил в силу после официального опубликования, за исключением положений о муниципальном образовании "Город Калуга", для которых установлены иные сроки вступления в силу. Опубликован: "Весть", №402–404, 29 декабря 2004 г. (Legislative Assembly of Kaluga Oblast. Law #7-OZ of December 28, 2004 On Establishing the Borders of the Municipal Formations Located on the Territory of the Administrative-Territorial Units of "Babyninsky District", "Borovsky District", "Dzerzhinsky District", "Zhizdrinsky District", "Zhukovsky District", "Iznoskovsky District", "Kozelsky District", "Maloyaroslavetsky District", "Mosalsky District", "Ferzikovsky District", "Khvastovichsky District", "City of Kaluga", "City of Obninsk", and on Granting Them the Status of an Urban Settlement, Rural Settlement, Urban Okrug, Municipal District, as amended by the Law #620-OZ of September 29, 2014 On Amending the Law of Kaluga Oblast "On Establishing the Borders of the Municipal Formations Located on the Territory of the Administrative-Territorial Units of "Babyninsky District", "Borovsky District", "Dzerzhinsky District", "Zhizdrinsky District", "Zhukovsky District", "Iznoskovsky District", "Kozelsky District", "Maloyaroslavetsky District", "Mosalsky District", "Ferzikovsky District", "Khvastovichsky District", "City of Kaluga", "City of Obninsk", and on Granting Them the Status of an Urban Settlement, Rural Settlement, Urban Okrug, Municipal District". Effective as of after the official publication, with the exception of the clauses regarding the municipal formation of the "City of Kaluga", for which different dates of taking effect are specified.).