The area of Valandovo was settled since the pre-historic period. It is believed that the per-historical settlement dates from the Bronze and Iron age (12th-7th century BC). Several Roman mosaics have been found in the several parts of the town, which proves that Roman settlement existed here in the ancient period.
The Slavic tribes have settled this area at the end of 6th and the beginning of the 7th century. The historians have mentioned this town in thr 10th century by the name Valander. The medieval town was built on the exact location of the town today. During the reign of the emperor Dusan, in 1349 the town was mentioned as Alavandovo, which ment town of flowers.
Many legends exists for the origin of the name. According to one of them, in the period after the settlement of the Slavs in the area, some wealthy priest live here, named Vlando. He built the settlement and the church. In honor of this benevolent, the settlement was called Vlandovo, and later Valandovo.
In a document from the Ottoman period in 1579, it is written that the town was an administrative seat of the Bojmija area, with 25 settlements. At the period, there were 180 houses of which 29 were Turkish.
According to the Turkish writer, who visited the town in the second half 18th century, Valandovo is a settlement surrounded with vineyards and woods, 150 houses, 900 inhabitants, bazzar of 50 stores, small mosque, bath, two inns and a big monastery with plenty of monks.
In 1900 the town had 200 households with 1,195 inhabitants, while in front of the First World War - 300 household and 1,800 inhabitants.
During the period of the Balkan and the First World War, Serbian, Greek and Bulgarian armies could be seen in the town. In the period of 1918-1941, the town was into the borders of Serbia and later Kingdom of Yugoslavia.
The Buglarians have conquered Valandovo during the Second World War and hold it until, November 6th 1944, when the regular units of the Macedonian army liberated the town.