Adolescents spend most of their daily time in school and performing school-related activities. Different aspects of their school experiences, such as school performance, psychological factors related to school, and structural factors, consistently impact adolescents' health and are likely to be intertwined with their sleep (i.e., quantity and quality, sleep disturbances). This systematic review aimed to comprehensively summarize the reciprocal and longitudinal associations between adolescents' sleep and multiple aspects of their school experience. Using multiple search strategies and applying a two-step selection process, 25 journal articles matched the eligibility criteria and were thus included in the review. The results highlighted the contribution of poor sleep quality and sleep disturbances in predicting longitudinal school experiences-related outcomes (i.e., decreasing school engagement and performance, and increasing school-related burnout, absenteeism, and bullying). At the same time, the results showed how experiences related to the school's psychological factors (e.g., high levels of school burnout and stressful environment) and structural characteristics (e.g., early school entrance time) affect youth sleep over time (i.e., decreasing sleep quality and quantity). These main findings provided novel insights into the bidirectional relationship between school experience and sleep health, highlighting the importance of more longitudinal research investigating all aspects of healthy sleep, including the size and direction of the association.