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On 1 June 2018, Gamakov signed a two year contract with Slavia Sofia.

On 13 March 2016, Gamakov played as a midfielder and scored one of the goals for the 3-1 win over Cherno More Varna.

In June 2016, Gamakov signed with Polish Ekstraklasa side Lechia Gdańsk. He spent the second half of the 2016–17 season on loan at Ruch Chorzów.

On 25 March 2016 Gamakov was in the starting lineup as a captain for the goalless draw with Wales U21. Four days later, on 29 March, he played in another goalless draw, this time against Luxembourg U21.

On 21 May 2016 Gamakov was in the starting lineup during the 0-1 defeat from France U21. On 6 June he played during the 0-2 defeat in a friendly game from Norway U21.

On 15 March 2015 Gamakov scored the first goal with a header for the important 2-0 home win over CSKA Sofia.

For Botev Plovdiv season 2015-16 was marked with a lot of changes of the managers. Despite this Milen Gamakov was regularly included in the starting lineup. In February 2016, due to a lot of injuries of his team mates, Nikolay Kostov started using Gamakov as a central defender.

Milen Gamakov missed the game against Wales U21 due to a ban. In the next game, on 9 June 2015, he played 90 minutes during the 1-0 win in a friendly game with Cyprus U21.

In September 2015 Gamakov was in the starting lineup for the 0-2 away victory over Romania U21 and the 3-0 home win over Luxembourg U21. He was the captain of the team and played 90 minutes in both games.

On 12 July 2014, Gamakov signed with Botev Plovdiv.

Milen Gamakov was named the second-place winner of the best youth player in A Grupa for season 2014-15. His teammate Tsvetelin Chunchukov won the first prize.

Antoni Zdravkov was appointed as manager of the Bulgaria national under-21 football team in October 2014 and he selected Gamakov as the new captain of the team.

Gamakov was included in the Bulgaria national football team for the first time on 6 November 2014. He remain and unused substitute during the 1-1 draw with Malta.

After end of season 2012–2013 and his good play at Neftochimic, he returned to Chernomorets. He made his debut for the team at first match of season 2013–14 against Cherno more Varna as a substitution.

Gamakov is youth player of Chernomorets Burgas since 2009. In 2013, he was sent on loan at Neftochimic Burgas till end of season 2013. He won promotion in A group with the team.

Milen Gamakov (Bulgarian: Милен Гамаков ; born 12 April 1994) is a Bulgarian professional footballer who currently plays for Slavia Sofia as a defender or midfielder.