Dimitar was born in Sliven (İslimiye), which was then part of the Ottoman Empire, to the family of the merchant Nikola Asenov and his wife Marinka Asenova.

It was active in the region of the Tundzha, Tvarditsa, Karlovo, Gabrovo and the well-known hajduk gathering place Aglikina Polyana.

Dimitar's band crossed the Danube at Vardim in a sail boat on 5 July and engaged in a battle with an Ottoman pursuing party of a thousand men in the vineyards of Karaisen, near Pavlikeni.

The remaining 58 members proceeded to the Balkan Mountains under the leadership of Hadzhi Dimitar, only to be crushed at Buzludzha Peak on 18 July.

After being defeated in this last battle, leader Hadzhi Dimitar, heavily wounded, was carried on a stretcher by his surviving comrades away from Ottoman army, up Mount Kadrafill, 3 km from the village of Svezhen.

The funeral service was conducted by the Bishop of Plovdiv Gervassius of Levkia, who made Hadzhi Dimitar a martyr.