Fyodor Olgovich was born in around 1360, the son of Oleg Ivanovich, the grand prince of Ryazan by his first wife, possibly named Vassa Anastasia Maria Ulyanaz.

He was brought up within the court of his father during a period of transition as the principality moved from Slavic paganism to the Russian Orthodox Church.

In exchange, Fyodor surrendered his right of independent relations with the Grand Duchy of Lithuania, the Golden Horde and other entities with which Moscow had relationships.

According to the chronicles of Tver, Fyodor called upon the support of Moscow and other Russian allies and fielded an overwhelming force of numbers.

However, this Fyodor rallied and within the year, at the Battle on the Smyadva River [ru] (Russian: битва на Смядве), he defeated Ivan Vladimirovich and retook Ryazan.

Although less than during the period between 1388 and 1402, when the desolation brought by the raids had left a huge mark on the southern lands of the principality, attacks by the Golden Horde continued throughout the century.

[9] He died the year after, in 1427, and was buried in the newly consecrated cathedral in Pereslavl, the first of the royal family of Ryazan to be interred there.