Educational leadership, as a multifaceted discipline, has undergone profound transformations from the early 20th century to the digital age. This study, employing a systematic review approach, examines the theoretical and practical evolution of the field across four key periods: the classical era, emphasizing efficiency and bureaucracy; the humanistic turn of the 1970s and 1980s, focusing on culture and values; the critical, feminist, and postmodern theories of the 1980s and 1990s, addressing inequality and power; and contemporary interpretations centered on technology, globalization, and systemic complexities. The findings indicate that educational leadership has evolved from a practice-oriented concept into a social, cultural, and ethical endeavor, necessitating a redefinition of the role of administrators as facilitators of learning and network leaders. Challenges in implementing these approaches include a lack of technological infrastructure and localized research. This study suggests that the development of educational leadership requires investment in technology, the enhancement of indigenous research, and the promotion of a culture of collaboration and justice to steer educational systems toward innovative and inclusive learning environments.