The oversized cargo transportation market in Poland actively participates in developing the economy, providing services necessary for implementing large infrastructure and industrial projects on a national and European scale. Development and functioning of this sector in the EU and globally requires overcoming many organisational, technical and administrative barriers and difficulties, and the authors of several publications indicate how these services are developing. The current study contains a detailed analysis of data from 2001-2022. The paper characterises the changes in particular years, indicating the main causes of the occurring processes, and defines the existing trends. It presents the legal framework that regulates the functioning of the domestic market. Moreover, it discusses the number of permits and the value of fees for issuing permits collected by the General Directorate for National Roads and Motorways (Generalna Dyrekcja Dróg Krajowych i Autostrad, GDDKiA) over two decades. The article also evaluates trends concerning the number of licenses more than 50% decrease compared to the maximum in 2008. It assesses the course of changes in values, which in 2021 reached their highest level during the period under assessment. Furthermore, it discusses the differences that occurred in the number of permits issued and applications submitted in the years 2014-2022. It describes the structure of the number of permits issued in categories IV-VII in 2014-2020 and categories III-V in 2021-2022. It characterises the course of the largest operation in the history of Polish road haulage - the transport of an abnormally-sized TBM (Tunnel Boring Machine) - in terms of requirements and problems that occurred during the preparation and fulfilment of this order and were typical for the functioning of the sector. The evaluation provides the basis for summaries and conclusions on the Development and condition of the oversized cargo transportation sector in Polish road transport sector.