The relationship between daytime sleepiness and heart rate asymmetry (HRA) during the transition from evening to night is crucial for understanding autonomic regulation and its implications for alertness. This study aims to investigate how daytime sleepiness influences HRA dynamics from evening to night and how situational sleepiness correlates with HRA metrics. HRA metrics were calculated at 8 P.M., 9 P.M., and 10 P.M. in 50 participants, categorized into 'Lower Normal' and 'Higher Normal' daytime sleepiness groups based on Epworth Sleepiness Scale (ESS) scores. Situational sleepiness was assessed using the Karolinska Sleepiness Scale (KSS) and Stanford Sleepiness Scale (SSS). The results demonstrated that individuals with 'Higher Normal' daytime sleepiness exhibited lower HRA metrics at 10 P.M. compared to those with 'Lower Normal' daytime sleepiness, supporting the suggestion that higher daytime sleepiness correlates with reduced parasympathetic activity and diminished autonomic responsiveness. Significant negative correlations between situational sleepiness and HRA metrics were observed in the 'Higher Normal' group, particularly with the SSS. Therefore, increased daytime sleepiness affects HRA dynamics by decreasing parasympathetic activity and altering autonomic regulation at the beginning of the biological night (10 P.M.). These findings suggest potential applications for enhancing drowsiness detection and managing fatigue in safety-critical environments.