From 977 to 997, he was a general under Roman I of Bulgaria, the second surviving son of Emperor Peter I of Bulgaria, and co-ruled with him, as Roman bestowed upon him the command of the army and the effective royal authority. As Samuel struggled to preserve his country's independence from the Byzantine Empire, his rule was characterized by constant warfare against the Byzantines and their equally ambitious ruler Basil II.

In his early years Samuel managed to inflict several major defeats on the Byzantines and to launch offensive campaigns into their territory. In the late 10th century, the Bulgarian armies conquered the Serb principality of Duklja and led campaigns against the Kingdoms of Croatia and Hungary. But from 1001, he was forced mainly to defend the Empire against the superior Byzantine armies.