[1] Born in Zabrčani, a village near Prilep, Dimoski started out at local club Pobeda, helping them win promotion to the Yugoslav Second League in 1959.
[5] After serving as an assistant to Dušan Nenković, Dimoski was appointed as manager of Radnički Niš in the summer of 1982.
He led the team to a fourth-place finish in his first season in charge, earning a spot in the 1983–84 UEFA Cup.
In 1989, Dimoski spent some time in Australia as manager of National Soccer League side Footscray JUST.
During the late 1990s and early 2000s, Dimoski served as manager of a number of Macedonian clubs, including Rabotnički and Bregalnica Delčevo.