One of the rare medieval institutions that represents an exception regarding the preservation of primary sources from medieval Slavonia is the cathedral chapter of Zagreb. That is why many studies have been published about this institution until now. However, the functioning of the economic system of the chapter of Zagreb in the 14th and 15th centuries has not been fully researched until now. This study analyzes and reconstructs how the canons and prebendaries of this chapter administered their estates around Zagreb, Varaždinske Toplice, Sisak and Veliki and Mali Gradac: how they managed the incomes and expenditures from these estates, as well as the population living on them. The establishment and maintenance of authority on the manors, as well as the relationship between the Chapter and the central government, was closely related to the collection of Church tithe, which is why this issue is being considered in particular. In moments of consolidation of power, the central government supported the efficient collection of this tax because it strengthened its authority on the periphery of the Kingdom. Finally, the concept of trust, increasingly applied in the last decade in historiography, gave an answer to the question of how the subjects themselves understood their place in the social hierarchy and on the estate. Did the chapter of Zagreb, as a lord, maintain its authority over its subjects mainly by coercion or by mutual trust in the 14th and 15th centuries? The most important issue under discussion is the reach of the process of rationalization and the development of the market economy. The thesis that is argued in the study is that the social structure and customs of that time influenced monetary practices, more precisely, prevented the overall transformation of the growing process of monetization.