In modern society, many workers struggle with sleep deprivation due to their work schedules and excessive workloads. Accurate self-awareness and self-monitoring abilities are crucial for workers to adopt risk-coping strategies and protective behaviors when fatigued. The current study examined the relationship between chronotypes and self-monitoring performance during 24 h of sleep deprivation. The study involved 26 male adults in a two-night experiment, and participants' diurnal preferences were evaluated using the Morningness-Eveningness Questionnaire (MEQ). Self-monitoring performance was calculated by comparing actual task performance with self-rated predicted or post-estimated performance in the psychomotor vigilance task (PVT) and Digit Symbol Substitution Task (DSST). The study found that task and self-monitoring performances in the PVT and DSST were maintained until around 4:00 h, after which they began to deteriorate. Individuals with a higher MEQ score, indicating a stronger tendency towards a morning type, showed inaccurate self-monitoring, particularly in the final quarter of the sleep deprivation experiment, due to overly optimistic predictions. However, only prediction accuracy and not post-estimation showed this correlation. This study highlights the importance of considering an individual's chronotype in workplace management, particularly in workplaces with irregular work timings, rotating shifts, and long working hours, to ensure better occupational safety.