The function of school leadership has been significantly changed by the multi-layered school context to meet the demands of stakeholders. Increasing autonomy and accountability pressures have made it difficult to maintain the balance of principals’ tasks, which gives rise to a variety of challenges. This study adopted a descriptive quantitative form of a systematic review to analyse 169 related studies about the challenges faced principals and research-informed coping solutions for such challenges published in the international journals indexed by the WoS, SCOPUS, and ERIC databases between 2001 and 2020. This analysis identified 734 contextual challenges, including challenges related to principals’ roles and actions (31%) influenced by institutional contexts (24%), socio-cultural contexts (11%), stakeholders (3.4%), and parents (5.2%). Additional contextual challenges were related to the leading staff (6%) and teachers (7.9%). Finally, 11.2% of the contextual challenges corresponded with concerns about student performance. This research highlights the need for modifying leadership preparation programs in a context sensitive manner, active participation of all stakeholders in setting school targets and methods for achieving them, and creating a supportive culture that encourages mutual progressive trust between governments, local communities, and school principals.