Sleep is a resource that has been associated with health and well-being; however, sleep insufficiency is common among adolescents. To examine how delaying school start time is associated with objectively assessed sleep duration, timing, and quality in a cohort of adolescents. This observational cohort study took advantage of district-initiated modifications in the starting times of 5 public high schools in the metropolitan area of Minneapolis and St Paul, Minnesota. A total of 455 students were followed up from grade 9 (May 3 to June 3, 2016) through grade 11 (March 15 to May 21, 2018). Data were analyzed from February 1 to July 24, 2019. All 5 participating schools started early (7:30 am or 7:45 am) at baseline (2016). At follow-up 1 (2017) and continuing through follow-up 2 (2018), 2 schools delayed their start times by 50 and 65 minutes, whereas 3 comparison schools started at 7:30 am throughout the observation period. Wrist actigraphy was used to derive indices of sleep duration, timing, and quality. With a difference-in-difference design, linear mixed-effects models were used to estimate differences in changes in sleep time between delayed-start and comparison schools. A total of 455 students were included in the analysis (among those identifying sex, 225 girls [49.5%] and 219 boys [48.1%]; mean [SD] age at baseline, 15.2 [0.3] years). Relative to the change observed in the comparison schools, students who attended delayed-start schools had an additional mean 41 (95% CI, 25-57) objectively measured minutes of night sleep at follow-up 1 and 43 (95% CI, 25-61) at follow-up 2. Delayed start times were not associated with falling asleep later on school nights at follow-ups, and students attending these schools had a mean difference-in-differences change in weekend night sleep of -24 (95% CI, -51 to 2) minutes from baseline to follow-up 1 and -34 (95% CI, -65 to -3) minutes from baseline to follow-up 2, relative to comparison school participants. Differences in differences for school night sleep onset, weekend sleep onset latency, sleep midpoints, sleep efficiency, and the sleep fragmentation index between the 2 conditions were minimal. This study found that delaying high school start times could extend adolescent school night sleep duration and lessen their need for catch-up sleep on weekends. These findings suggest that later start times could be a durable strategy for addressing population-wide adolescent sleep deficits.