Caffeine consumption has been linked to poor sleep health in adolescents, but it is unknown whether poor sleep predicts caffeine consumption, and/or whether caffeine consumption predicts poor sleep, particularly when sleep is measured objectively. Data were collected from a micro-longitudinal sub-study of the age 15 wave of the Fragile Families and Child Wellbeing Study (n = 589). Adolescents wore an actigraphy device and completed daily surveys for ~1 week. Daily surveys assessed subjective sleep quality and caffeinated beverage consumption (0 = no caffeine, 1 = any caffeine). Separate mixed models assessed whether actigraphy-measured sleep duration, timing, maintenance efficiency, and subjective quality predicted next-day caffeinated beverage consumption within and between adolescents. Variability (standard deviation) of sleep duration and timing, sleep regularity index, and social jetlag were tested as additional between-person predictors. Lagged models tested whether daily caffeinated beverage consumption predicted sleep that night (n = 458). Adolescents with more variable sleep duration and midpoint had higher average odds of consuming caffeinated beverages compared to others. After adolescents consumed ≥1 caffeinated beverage, they had later sleep onset that night and wake time the next morning than usual versus when they did not consume caffeine. Curbing caffeinated beverage consumption may aid in the maintenance of regular sleep schedules and advance sleep timing in adolescents.