[1] Shokolarov began his career with Pirin Gotse Delchev before moving to Svetkavitsa in 2008.

After four and a half seasons in Svetkavitsa, his contract was terminated by mutual consent in December 2012 and Shokolarov joined Montana, signing a one-and-a-half-year deal.

[2] In the summer of 2016, Shokolarov signed with Ludogorets Razgrad II since the team wanted an experienced players in Second League.

On 20 August 2016, because Georgi Dermendzhiev decided to give a rest to some of the players before the upcoming Champions League play-off match, he made his debut for the first team of Ludogorets and scored a goal.

[5] He was part of the CSKA 1948 team between January and late April 2020, appearing in two official games.