The regeneration of oak forests in the hilly and mountainous areas is one of the most serious and complex problems forestry practitioners face in Serbia. The success of regeneration depends on the individual or combined (often synergistic) influence of numerous biotic, abiotic, and management factors. While there is significant knowledge and experience about this process in practice so far, there is still great uncertainty regarding its proper execution and control over the influencing factors. The paper critically evaluated the available literature and current experiences from practice through a questionnaire. A comprehensive literature search was conducted, taking into consideration various databases and search engines, mostly composed of peer-reviewed publications from ISI-listed journals. A total of 187 papers were included in the base. Aiming to better understand the current state and the main problems in the regeneration of hilly-mountainous oak forests in Serbia, surveys were performed among forest practitioners. Based on this, the paper synthesized the current knowledge and addressed future perspectives in hilly-mountainous oaks management. More specifically, the factors that dominantly influence the regeneration process, their modes of action, behavior in the case of modifications, as well as the possibilities of their interaction are defined. The success of regeneration is determined by canopy openness, microclimatic conditions, presence of competitive vegetation, initial number of seedlings, and seedling growth and health, as revealed in the literature. The proposed methods for more successful regeneration and restoration of oak forests, include producing high-quality seedlings, using advanced weeding methods, developing a specific strategy for restoring native oak forests, assessing genetic resources and long-term monitoring. Overall conclusion of the conducted literature analysis is that there is a great need for conducting further long-term research on improving the regeneration systems in hilly-mountainous oak forests in Serbia.