Youth career Born in
Kyustendil, Dimitrov started his career in the local team
Velbazhd Kystendil. He became one of the first players to join the newly created team FC Buzlodzha Kyustendil, which later merged with Velbazhd Kyustendil. From Buzlodzha Oleg was attracted to the 31 time champions of Bulgaria -
CSKA Sofia. He became a champion with the U17 league. In 2012, he moved to the Bulgarian champions
Ludogorets Razgrad.
Ludogorets Razgrad In 2012 Dimitrov joined the youth system of
Ludogorets Razgrad. In 2014, he played for Ludogorets U19 in the
UEFA Youth League, being a titular in all of the 6 matches. In 2015 Dimitrov became champion with Ludogorets in the U21 league where he served as a vice-captain of the team. He also scored 3 goals in the league. From the 2015/16 season Ludogorets got the chance to have second team in
B Group and Oleg was promoted to the newly created
Ludogorets Razgrad II. He made his debut for the team on 2 August 2015 in a match against
Pirin Razlog, losing 1:0. On 23 September 2015 he made his debut for Ludogorets first team in a match against
Lokomotiv 1929 Mezdra for the
Bulgarian Cup won by Ludogorets by 5:0. He completed his debut for the club in
A Group on 27 May 2016 in a match against
Botev Plovdiv. Dimitrov started the 2017-18 season in
Ludogorets II playing in the first match of the season against
Lokomotiv 1929 Sofia. ==International career==