Jakovenko learned chess from his father at the age of three years and was later coached by Garry Kasparov's former trainer Alexander Nikitin.

He finished first in the Anatoly Karpov International Tournament (pl) in Poikovsky, Khanty-Mansi Autonomous Okrug, Russia in 2007, 2012[5] and 2018.

[7] In the same month Jakovenko competed at the Dortmund Sparkassen Chess Meeting, finishing shared second with Peter Leko and Magnus Carlsen, fourth on tiebreak, with a score of 5½/10, one point behind Kramnik.

[15] In 2015 Jakovenko tied for first place with Hikaru Nakamura and Fabiano Caruana in the last stage of the FIDE Grand Prix series, held in Khanty Mansyisk, scoring 6½/11 points.

[20] In 2018, Jakovenko tied for 1st - 2nd place in the Superfinal of the 71st Russian championship in Satka, Chelyabinsk Oblast.