Repeated Route Naturalistic Driving Dataset (R2ND2) is a dual-perspective dataset for driver behavior analysis constituent of vehicular data collected using task-specific CAN decoding sensors using OBD port and external sensors, and (b) gaze-measurements collected using industry-standard multi-camera gaze calibration and collection system. Our experiment is designed to consider the variability associated with driving experience that depends on the time of day and provides valuable insights into the correlation of these additional metrics on driver behavior.