Little research has explored the challenges of difference and difficulty to principal leadership in changing school contexts. This paper explores two Chinese principals’ journeys to enact different leadership approaches to overcome these challenges during a time of massive education reform. Three specific questions are asked: What challenges do the principals face in diverse student populations? What leadership practices do the principals adopt to support the learning development of these students? What support do the principals need most to enact this leadership? This cross-case study, conducted in Hong Kong, finds that principal leadership that focuses on inclusion is important in efforts to overcome these challenges, with innovative and flexible interventions to ensure equality in student learning development. Despite this, they need support from every part of the school community: the school sponsoring body, the teaching team and parents. The implications of these findings for interpreting the meanings of principal leadership for inclusion are also discussed. Copyright © 2018 Informa UK Limited, trading as Taylor & Francis Group.