In developing countries, road traffic crashes involving pedestrians have become a foremost concern. At present, road safety assessment plans and selection of interventions are primarily restricted to traditional approaches that depend on the investigations of historical crash data. However, in developing countries such as India, the availability, consistency, and accuracy of crash data are major concerns. In contrast, proactive approaches such as studying road users' risk perception have emerged as a substitute method of examining potential risk factors. An individual's risk perception offers vital information on probable crash risk, which may be beneficial in detecting high-risk locations and major causes of crashes. Since the pedestrian fatality risk is not uniform across the urban road network level, it may be expected that pedestrians' perceived risk measured in terms of “crossing difficulty” would also vary across the sites. In this perspective, the present paper establishes a mathematical association between the pedestrians' perceived “crossing difficulty” and actual crashes. The model outcome confirms that pedestrians' perceived crossing difficulty is a good surrogate of fatal pedestrian crashes at the intersection level in Kolkata City, India. Subsequently, to examine the impact of traffic exposures, road infrastructure, land use, spatial factors, and pedestrian-level attributes on pedestrians' “crossing difficulty”; a set of Ordered Logit models are developed. The model outcomes show that high vehicle and pedestrian volume, vehicular speed, absence of designated bus stop, the presence of inaccessible pedestrian crosswalk, on-street parking, lack of signalized control (for both vehicle and pedestrian), inadequate sight distance, land use pattern, slum population, pedestrian-vehicular post encroachment time, waiting time before crossing, road width, and absence of police enforcement at an intersection significantly and positively increase pedestrian's crossing difficulty at urban intersections. To end, the model findings are advantageously utilized to develop a set of countermeasures across 3E's of road safety.