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Previous studies have revealed that students who work and study build up sleep deficits during the workweek, which can trigger a sleep rebound during days off. The objective of this study was to investigate the impact of working/non-working on sleepiness during days off among high school students. The study population, aged 14-21 years, attended evening classes in São Paulo, Brazil. For the study, the students completed questionnaires on living conditions, health, and work; wore actigraphs; and completed the Karolinska Sleepiness Scale (KSS). To predict sleepiness, a logistic regression analysis was performed. Excessive sleepiness was observed on the first day off among working students. Results suggest that working is a significant predictor for sleepiness and that two shifts of daily systematic activities, study and work, might lead to excessive daytime sleepiness on the first day off. Further, this observed excessive sleepiness may reflect the sleep debt accumulated during the workweek.