This chapter explores the integration of Entrepreneurial Orientation (EO) and Green Supply Chain Management (GSCM), highlighting how firms can leverage EO—characterized by innovativeness, proactiveness, and risk-taking—to enhance sustainability within their supply chains. The discussion covers key concepts, theoretical foundations, and the impact of EO on GSCM, emphasizing the role of innovation and strategic alignment in achieving environmental, economic, and social sustainability outcomes. Challenges and barriers, such as organizational culture, financial constraints, and regulatory pressures, are analyzed, along with strategic implications for competitive differentiation, cost efficiency, and risk management. The chapter also identifies emerging trends, including digital transformation, the circular economy, and sustainable sourcing, offering directions for future research. Ultimately, the chapter underscores the importance of integrating EO with GSCM as a transformative approach for businesses aiming to lead in sustainability while driving long-term success.