On Wednesday, 4 September, the Draw for OLIMP Cup of Russia 2019/20 Round of 32 ties took place in Moscow. FUR General Secretary Alexander Alaev; RPL, FNL and PFL Presidents: Sergey Pryadkin, Igor Efremov and Andrey Sokolov took part in it. As well as Match TV experts: Andrey Tikhonov, Ruslan Pimenov, Evgeny Aldonin and Alexey Smertin.

According to the Draw results the ties were drawn the following way:

 Enisey – Zenit
Alania – PFC CSKA
Baltika – Lokomotiv
Nizhny Novgorod – Krasnodar
Torpedo – Krylia Sovetov
Chayka – Ufa
Tom – Tambov
Shinnik – Sochi
KAMAZ – Spartak
Fakel – Arsenal
Chertanovo – Orenburg
SKA-Khabarovsk – Akhmat
Mordovia – Rostov
Luch – Dynamo
Chernomorets – Ural
Khimki – Rubin

Round of 32 matches will be played on 25 and 26 September 2019, the exact dates will be confirmed in due course. For RPL clubs all matches will be played away.