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A product of the Omsk club Neftyanik, he moved to the leading club of his city, Irtysh, in 2012, where he made his debut in adult football, spending 2.5 seasons in the Second Division.
In early 2016, he went to Fakel, which was playing in the First League at the time, and won the 2017 FNL Cup with them. At the same time, he first crossed paths with Dynamo, making a significant contribution to his team's dry victory in Khimki. In 2018, he went through the summer training camp with the white-blues under the leadership of Dmitry Khokhlov and even scored a goal against Bulgaria's Chernomorets, but eventually returned to Fakel.
After another season in the FNL, Osipenko moved to Tambov and made his debut in the RPL at the age of 25. In the 8th round match against Akhmat, he scored his first goal at the highest level (before that, he had 17 goals for Irtysh and Fakel).
In January 2020, Maxim was promoted to Rostov coached by Valery Karpin, signing a 4.5-year contract, and was appointed team captain in 2021. In September of the same year, he made his debut in the national team.
Osipenko was a regular penalty taker for Rostov and in the 2024/25 season, he repeated the Russian championship record for goals in a season among defenders, scoring 9 goals. Thanks to this, he entered the top 10 scorers of Rostov in the history of the Russian championship - 23 goals in 146 matches.
In June 2025, Maksim signed a long-term contract with Dynamo.
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