In 1935, Gerstenfeld shared 4th with Jakub Kolski, behind Izaak Appel and Achilles Frydman, in Łódź (quadrangular).
In March 1940, he took 4th in Lviv (Western Ukrainian championship, Abram Khavin won).
In 1940, he tied for 16-17th in Kiev (the 12th Ukrainian Chess Championship, Isaac Boleslavsky won).
In January/February 1941, he won ahead of Appel, Friedman, Emanuel Rubinstein and Schächter, in the Lviv City championships.
In June 1941, he was at 3rd place in Rostov-on-Don (the 13th USSR-ch semi-final), when Operation Barbarossa, the German attack on the Soviet Union, interrupted the event.