Leon Konstantinovsky played at Maccabi Tel Aviv as a midfielder during the 74/75 and 75/76 seasons scoring 4 goals in 20 games in all competitions. Konstantinovsky began his playing career at Maccabi Ramat Amidar from which he joined Maccabi Tel Aviv at the age of 28 before returning to Amidar two years later.

After ending his playing career, Konstantinovsky began a successful coaching career with Maccabi Ramat Amidar, Hapoel Ramat Gan, Maccabi Yavne, Hakoah Maccabi Ramat Gan, Bnei Yehuda, Beitar Tel Aviv, Maccabi Netanya, Maccabi Petah Tikva Maccabi Jaffa and specialized mostly in guiding teams to promotion, achieving that with no less than 7 clubs during the 80’s.