He started playing football in a local club in Skopje named FK Jug, before moving to Gragjanski Skopje in 1938. In 1941, during World War II and the Axis invasion of Yugoslavia, most of the region of the then Vardarska Banovina was occupied by the Bulgarian forces and in that period, Gragjanski was renamed to Makedonija Skopie. The club finished in second place in the 1942 Bulgarian State Championship, and during this period, Simonovski played two matches for the Bulgarian national team (as Kiril Simeonov).[2] At the end of the war, Simonovski moved to Belgrade and signed with newly formed FK Partizan where he will play all the way until 1950, winning two national championships and one cup.
International
It was in this period that he became the first Macedonian to play for the post-1945 Yugoslavia national team, having played a total of 10 matches and scored once.[3]
Managerial career
After retiring he became a coach. He coached FK Partizan, FK Vardar and Olympiacos F.C. among several other clubs in Yugoslavia, Greece and Cyprus.
