Yambol has been inhabited since Neolithic times and was an important city in ancient Thrace and the First Bulgarian Empire. It grew significantly as a trade and military center under Roman Emperor Diocletian and Bulgarian rulers Boris I, Simeon I, and Kaloyan. While the population exceeded 90,000 in the late 20th century, it has since declined to around 74,000 as many migrated to larger cities due to economic difficulties in the 1990s.