As a child, Elena Mikhailovskaya was enjoying active sports, but at the age of 15 health issues forced her to settle down.

Starting from 1969 she was playing for the Moscow club Lokomotiv Moscow, and the same year she won the senior title of the Soviet Union champion in Russian checkers, defeating in the last game of the tournament the previous holder of the title, Iraida Spasskaya, and then winning the gold medal barrage against Janina Augustinaite.

She then went to hold the title for three more years in a row, establishing the all-time Soviet record.

In 1973, she won a prestigious international tournament in Amsterdam which was retroactively considered to be first unofficial world female championship.

Among these, her 1975 victory was considered the most special, since Mikhailovskaya has finished it with a nearly perfect score, drawing only the last game against Lenie Toonen-Geurts after winning eight in a row.