11^th Century

The fair was very popular not only with people from Skopje and the surrounding villages, but also with visitors from other cities in Macedonia and other parts of the Balkans. Improvised counters offered a variety of goods produced by trading and craft workshops  in several Romaoian cities, especially in Thessaloniki and Constantinople.

Later on, a weekly market was also approved. Located on the same spot where the fair was organised, i.e. on the monastery meadow, the weekly market took place Fridays. It was divided into two sections -- one selling agricultural and garden products, and the other one for cattle (horses, cows, sheep, and goats).

12^th Century

Traders soon realised that they could not sell all their goods on the market in one day. They were therefore compelled to stay overnight on the monastery meadow and make improvised covers to protect their goods. The monastery managers and tax collectors, however, did not allow the erection of any kind of permanent structures that would impede the liberal use of the surrounding space. The traders then began building improvised stores for their unsold goods in a wall-protected area of the city next to the market, which was being locked overnight. The number of these stores gradually increased with time, moving toward the city. This area was not under the monastery's jurisdiction, so the city authorities also started charging the traders a certain tax for their edifices. Rather than paying tax twice, both to the city for keeping their goods there and to the monastery for selling the goods on the market (the monastery meadow), the traders started building more solid buildings where they not only stored, but also began to sell their goods, so that they stopped going to the market altogether. This marked the initial stage of the development of craft shops in Skopje's Old Bazaar.

13^th Century

With the increased need of selling and storing space for more and more valuable goods, the construction of a special monumental building for this purpose -- a shopping centre like the already existing ones in the Romaoian metropoles was imminent. This building can be clearly seen on a 15th-century engraving. It was a solid building with 15 large extended arcs in a row with a space underneath, covering an area of more than 1,200sq.m.

Despite the construction of this centre, trade was still much more present on the market (the former monastery meadow), which kept the continuity of the weekly market and the annual fair. At the same time, the complex of improvised space and small shops toward the city area was getting bigger. With time, these small trade and craft shops began diverging and grouping according to the type of merchandise they were producing. Later, these were to become separate markets altogether.

14^th & 15^th Centuries

During the Ottoman period, the trade and crafts remained in the hands of the Macedonian population, as well as in the hands of earlier settlers, including Jews, Armenians, and Dubrovnikans. This saved the city’s business and trade from being assimilated. This period was very prolific in the construction of numerous Islamic religious and secular buildings. The city, fortified with many caravanserais and inns, with the renovated Romaoian and newly built Bezisten of Isak Bey, with an elaborate system of various shops and production workshops grouped in specialised markets, progressed very fast toward becoming a rich trade centre. Besides local merchants, a large number of traders from various Mediterranean cities, especially Venice and Dubrovnik, could be seen in Skopje. The Jewish and the Armenian colonies grew considerably in this period and became a significant factor in the business and trade development.