Contemporary cities face complex challenges, including climate change, aging infrastructure, and socio-spatial inequalities, to which conventional urban development approaches are no longer able to adequately respond. These conditions highlight the need to rethink conventional development models and move toward more comprehensive and forward-looking approaches. In this context, the concept of the regenerative city has emerged as a novel framework emphasizing the capacity of cities to create new social, economic, and ecological value. This study aims to analyze the conceptual transformation from smart urban regeneration to regenerative cities and identify its implications for entrepreneurial ecosystems. Using an integrated bibliometric and systematic literature review approach, 89 articles indexed in the Scopus database and published between 2015 and 2025 were analyzed. The findings indicate that the literature in this field is shifting from a technology-driven and optimization-oriented approach toward regenerative approaches, the circular economy, nature-based solutions, and smart governance. Co-authorship networks reveal fragmented scientific collaboration and weak interdisciplinary linkages, while co-citation analysis indicates the gradual emergence of a shared theoretical framework centered on regeneration and critiques of the technology-driven smart city approach. From this perspective, the study connects the emerging literature on regenerative cities with entrepreneurial ecosystem research, thereby highlighting the gap between these two streams of scholarship. The findings show that entrepreneurial ecosystems can serve as a mechanism linking technology, governance, and urban value creation, provided that they move beyond a purely profit-oriented logic toward regenerative entrepreneurship. By revealing the knowledge structure, theoretical gaps, and emerging research directions, this study provides a foundation for advancing future research on regenerative cities and the role of entrepreneurial ecosystems in achieving their objectives.