[1] Dimitrija Čupovski was born in the village of Papradište in the Ottoman Empire (now part of Čaška Municipality, North Macedonia).

According to Shaldev, a member of the Secret Macedonian-Adrianopolitan circle and IMRO, the main ideologists under whose influence Čupovski had fallen, were the Serbian professors Stojan Novaković, Jovan Cvijić and Aleksandar Belić.

[3][4] When in 1905 Čupovski tried to organize for the first time a pan-Macedonian conference in Veles, he was expelled from the town by a local chief of IMRO Ivan Naumov,[5][6] and was threatened with death for his pro-Macedonian and anti-Bulgarian ideas.

[9] Some Bulgarian researchers also suppose that Čupovski was a marginal figure and Serbian agent on a service of the Russian Imperial Ministry of Foreign Affairs.

[10][11] After the outbreak of the Balkan War in 1912, Čupovski arrived on November 17 in Sofia, where he met with a part of the Macedonian emigration, but without much success.

Čupovski convinced them to send representatives to the London peace conference to try to preserve the integrity of the region of Macedonia, but this attempt was also unsuccessful.