Topolovgrad and the surrounding area have been inhabited since ancient times, as evidenced by the dolmens found at Hlyabovo and the Paleokastro fortress that may have been built by the Thracians.
Until early 20th century, the town was predominantly inhabited by Greeks (96 percent) and hosted Greek schools and churches. Although a Greek majority town, after 1906, the Bulgarian government appointed the first Bulgarian mayor. From 1906 to 1925, about 4,000 Greeks left the town and its surroundings and settled in Greek Macedonia. They were replaced by groups of Bulgarian refugees from Western Thrace, Eastern Thrace, Asia Minor and Macedonia.