Area of the present Olšanské Square was settled in 1910. Then the name Radešín Square had its origin, after Vilém of Radešín (Hradešín), who acquired the village of Olšany, or as it used to be said Volšany, in 1546. It was situated east of Prague, of course far behind the fortifications and it is firstly mentioned in 1394.

In 1930 the square got name Olšanské and it has been valid till now. Since 17th century Olšany was the property of Old Prague Town. It established Prague central cemeteries in local lands in the plague periods and after intellectual Emperor Joseph II forbade burying people in cemeteries in the inner city in 1787 and after he abolished them at all. The cemeteries were extended further and it is estimated that more than million funerals have been realized there. Cemeteries in Olšany are the last resting places for many outstanding personalities and also they are big gallery of funeral sculptures.

The first burial site was made there on the occasion of huge plague epidemic in 1680. During 1680-1682 a sacral baroque central building was constructed there by Jan Hainric, perhaps according to design by Jean Babtiste Mathey. The church was consecrated to the anti-plague patrons, St Roch, Šebestian and Rosalie.

Large part of the northern side of Olšanské Square is taken by a new modern multi-purpose building constructed in 1988-1994. Investor was the Central Committee of Trade Unions. Among others there are hotel and restaurant; part of the building is leased by Central-European University.

Public traffic bus line is going through Olšanské Square and a tram line is divided there in the direction away from the centre. One branch is running to Flora along the cemeteries in Olšany, the latter is going to the goods-station in Žižkov.