Dimitrov began his career in 2004 with Makedonska Slava and later played with PFC Pirin Blagoevgrad and FC Septemvri Simitli.

[5] After Belasitsa was relegated to the Bulgarian B Professional Football Group he went overseas to Canada to sign with the Serbian White Eagles of the Canadian Soccer League.

[7] During his tenure with the White Eagles, he managed to achieve an International division title and reached the CSL Championship finals.

[12] In the club's debut season the team finished tenth in the overall standings and missed the final postseason berth by a goal difference.

[15][16] In 2021, he assisted Scarborough in securing the CSL Championship against FC Vorkuta in the playoffs.