Ivaylovgrad (Bulgarian: Ивайловград, "city of Ivaylo", Greek: Ορτάκιοϊ, Turkish :Ortaköy, "Middle Village") is a town in Haskovo Province in the south of Bulgaria set near the river Arda in the easternmost part of the Rhodope Mountains, and is the administrative centre of the homonymous Ivaylovgrad Municipality.

Byzantine eparchial lists from the time of the 9th-10th century mention a bishop's centre by the name of Lyutitsa on the site of present-day Ivaylovgrad.

Information about the town during the Ottoman rule of Bulgaria is scarce, but it was the centre of a kaza under the name of Ortaköy in Edirne Province.

Much of the Bulgarian population moved from the region due to organized robberies and internecine wars in the empire.

Despite the Liberation of Bulgaria in 1878 and the Unification in 1886, the town remained a part of the Ottoman Empire until the Balkan Wars in 1912–1913 and suffered greatly from bashi-bazouk attacks.