Immediately after the liberation of Skopje, in March 1945, a decision was made to establish a library in the city. After previously completed preparations, on November 15th of the same year, the library began its cultural and educational activities, with an initial book fund of 3,500 publications, of which 500 books were children's literature. Part of the book fund was taken over with strict selection from the pre-war library that operated in Skopje from 1935 to 1940, and part was a gift from the citizens of Skopje. From its founding until the end of 1955, the library functioned as the City Library, and from 1956, when it was declared a District Library, it was renamed to National Library of the Skopje District, tasked to serve as a library center for the district.

The period from 1953 to the end of 1955 is a period when all libraries in Skopje are under joint management, i.e. all are under the management of the City Library. This means that the City Library was the main carrier for the development of the library activities in the library clones in the city. In 1962, the library was declared the main library in the area of ​​the city of Skopje, whereby the role of the library center was taken over by the main service, which takes care of the development of the library network in a planned and organized manner. As a main institution, the Library invests great efforts in expanding the library network of regional libraries, in urban and rural areas. It formed its own library network with the opening of the first library clones in the villages: Studenichani, Bulachani, Kuchevishte and the regional library in the residential area of Taftalidze known as "Dimitar Vlahov".

The library also carries out its activities through the mobile library, established in 1972 with an initial book fund of 8,286 books. This library, wanting to bring books closer to the reader even in the most remote places, manages to serve 14 villages in the wider city area. The book fund of the mobile library has over 60,000 library units, and about 3,000 members are served annually.

On 18.02.1974, the City Library “Brakja Miladinovci” – Skopje made a decision to merge with the other independent libraries of the municipality of the city of Skopje and to form the “Brakja Miladinovci” library. Thus, the City Library “Brakja Miladinovci” – Skopje merged with the libraries “Cvetan Dimov” – Skopje, “Strasho Pindzur” – Skopje and “Drugarche” – Skopje. Today, the City Library “Brakja Miladinovci” consists of three central libraries and 20 library clones.

The library has been moved several times during its existence. At first, it was located in a part of the building of the “Goce Delchev” Primary School in an area of ​​200 m2. However, due to the permanent increase in the book collection and the expansion of the library’s activities, the space became a serious obstacle to its further development. Due to the damage caused by the earthquake in 1964, the library was moved to a modular cabin of 520 m2 in the residential area “Karposh 1”, where it remained until 1973, when the new library building was built, in which the City Library “Brakja Miladinovci” still carries out its activities today.

The successful results of the Library in the past period have also been contributed by the qualitatively resolved spatial issue. The facility was purpose-designed and built for carrying out library and information activities and is one of the most functional library spaces in North Macedonia.

Back in 1945, the Library carried out its activities with a total of 4 employees, of whom 1 had higher education, 2 had secondary education and 1 had primary education. However, today the library staff in the Library has changed significantly both in terms of number of employees and education, and is qualified and professionally trained to perform even the most complex professional library processes.

The entire book collection is processed according to international standards for processing monographic and serial publications. In addition to the mandatory alphabetical and specialist catalogs according to the National Library of Macedonia, the Library also produces a central catalog, which provides a complete insight into the state and structure of the book collections in all regional libraries.

The City Library "Brakja Miladinovci", realizing the need for automated processing of library material, was equipped with computer and communication equipment and in 2004 joined the Cooperative Online Bibliographic System and Service (COBISS). For the successful implementation of these processes, part of the library staff attended a course on mutual cataloguing, organized by IZUM for all libraries using COBISS. Equipped in this way, the library represents a modern library-information center, which greatly contributes to the modernization and development of library activities in the city of Skopje, but also more broadly in the Republic of North Macedonia.