This paper investigates the evolution of leadership for learning that has occurred in four secondary schools located in disadvantaged contexts in the province of Granada (Spain) over a period of 2 years, performing a comparative analysis on the values, qualities and strategies that characterize their principals during the academic years 2013-2014 and 2015-2016. The investigation uses case studies and conducts interviews with principals, teachers and education administrators. It is supported by the group-case method, as well as the longitudinal prospective method. The results show that only one of these principals has maintained a leadership aimed at learning and achievement of all students in the school, at the same time as students' academic results have been improving. This paper concludes by providing information on values, qualities and strategies of successful leadership in disadvantaged contexts in Spain that distinguish them from other less successful leaders.