This study aimed to investigate sleep patterns in adolescent males over a 12-week period (a 10-week school term and pre and post term holidays). Intensive longitudinal design, with sleep data collected daily via actigraphy for 81 consecutive days. Five Secondary Schools in Adelaide, South Australia. Convenience sample of 47 adolescent males aged 14 to 17 years. Daily sleep duration, bedtimes, rise times, and sleep efficiency were collected via actigraphy with all (except sleep efficiency) also measured by sleep diary. Mood was measured weekly with Depression Anxiety Stress Scale-21 (DASS-21) and weekly wellbeing with the Satisfaction with Life Scale (SWLS). Age, body mass index, self-reported mood, life satisfaction, and chronotype preference assessed at baseline (pre-term holiday week) were included as covariates. Dynamic Structural Equation Modeling indicated significant but small fixed-effect and random-effect auto-regressions for all sleep variables. Collectively, these findings demonstrate day-to-day fluctuations in sleep patterns, the magnitude of which varied between individuals. Age, morningness, and mood predicted some of the temporal dynamics in sleep over time but other factors (BMI, life satisfaction) were not associated with sleep dynamics. Using intensive longitudinal data, this study demonstrated inter-individual and intra-individual variation in sleep patterns over 81 consecutive days. These findings provide important and novel insights into the nature of adolescent sleep and require further examination in future studies.