Chronic pain is a common and disabling condition in adolescents. Disturbed sleep is associated with many detrimental effects in adolescents with acute and chronic pain. While sleep and pain are known to share a reciprocal relationship, the sleep-pain relationship in adolescence warrants further contextualization within normally occurring maturation of several biopsychological processes. Since sleep and pain disorders begin to emerge in early adolescence and are often comorbid, there is a need for a comprehensive picture of their interrelation especially related to temporal relationships and mechanistic drivers. While existing reviews provide a solid foundation for the interaction between disturbed sleep and pain in youth, we will extend this review by highlighting current methodological challenges for both sleep and pain assessments, exploring the recent evidence for directionality in the sleep-pain relationship, reviewing potential mechanisms and factors underlying the relationship, and providing direction for future investigations. We will also highlight the potential role of digital technologies in advancing the understanding of the sleep and pain relationship. Ultimately, we anticipate this information will facilitate further research and inform the management of pain and poor sleep, which will ultimately improve the quality of life in adolescents and reduce the risk of pain persisting into adulthood.