The study was designed to compare and study to what extent the Underpasses and Overpasses are effective among pedestrian in different urban contexts in Sri Lanka and characteristics improve the increment of utilization of Underpasses and Overpasses. The study focuses on two Underpasses and two Overpasses. The two Underpasses are Kandy and Borella Underpasses. Panadura and Maradana are the two Overpasses. The methodology of the study comprised of On-site observations, Oral interview questionnaire survey and Semi-structured interview. The data were analyzed by using frequency analysis, correlation analysis and content analysis aided by the SPSS software and MS excel. The findings on factors influencing the effectiveness of Underpass/Overpass showed that the most influencing factor for the effective utilization of Underpass/Overpass is that the “Self-enforcement feature”, while least cited factor is the “Attractiveness”. In addition, the effectiveness level revealed that more effectiveness towards Underpasses than Overpasses and Underpasses suits for commercial area, Transit need areas while Overpasses suits for School/college areas. Furthermore, the findings show that the Trip purpose and Location, Location & Time, Trip purpose & Time, Convenience and Comfort, Comfort and Personal safety have strong positive relationship on each other contributes for the effectiveness of the Underpass/Overpass. The study suggests that use or non-use of Overpass/Underpass is depending on attitude and behavioral pattern of pedestrians. Moreover, the study provides recommendations on towards enhancing maximum utilization. Accordingly, the results of the study provide a basis for planners, architects, developers and policy makers for the future design of effective Underpass/Overpass.