In 1927 he was involved in the Skopje Student Trial, during which he was tortured by the Serbian police,[3] but was released without charges due to lack of evidence.

After becoming a high school professor, he worked in Belgrade, Svilajnac, Čačak, Bijeljina, Štip, Smederevska Palanka, Ćuprija and Skopje.

[1][2][5] In April 1944 he became a member of the Initiative committee for the organization of the Antifascist Assembly of the National Liberation of Macedonia (ASNOM).

In June, Čučkov, along with Metodija Andonov - Čento and Kiril Petrušev met with Josip Broz Tito on the island of Vis for consultations due to their activity.

However, due to his agitation for an independent and united Macedonia, his stances were deemed nationalist, separatist and anti-Yugoslav, and he was removed from the post.

He is the author of several university and high school textbooks, manuals and research materials in the field of history, geography, economy, folklore, ethnography and education of the SR Macedonia.