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The earliest known sources that describe the existence of a merchant quarter on the bazaar's territory date back to the 12th century. During Ottoman Rule of Skopje, the Old Bazaar developed rapidly to become city's main centер of commerce. The Ottoman history of the bazaar is evidenced by roughly thirty mosques, numerous and hans, among other buildings and monuments. The bazaar was heavily damaged by earthquakes that occurred in 1555 and 1963, as well as during the First and the Second World Wars and faced various
rebuildings following these events. Ottoman Arhiceture is predominant in the Old Bazaar, although remains of Byzantine architecture evident as well, while recent reconstructions have led to the application of elements specific to modern architecture. Many of the historic buildings of the bazaar have been transformed into museums and galleries. It is, however, still home to several active mosques, turbes, two churches and a clock tower, that, together with the buildings of the Museum of Macedonia and the Museum of Modern Art, form the core of the modern bazaar.
On 13 October 2008, the Macedonian Parliament adopted a law recognizing the Old Bazaar as cultural heritage of particular importance for the country to be permanently protected. In early 2010, the Macedonian Government began a project for the revitalisation of the Old Bazaar, which includes the restoration of several objects and aiming a further economic and cultural development of the site.