Pedestrians are considered as one of the most vulnerable road users in less developed countries (LDCs). Yet, pedestrian safety remains poorly addressed in both urban and rural transportation plans in most LDCs. Since most pedestrian injury severity studies are conducted in developed countries, this study fills the gap with an inquiry focused on a highly urbanized region of an LDC that faces a rapid increase in car ownership and increasing pedestrian-related traffic injuries, documenting specific pedestrian safety issues and providing guidance for injury prevention measures in such places. Using the Metro Manila Accident Reporting and Analysis System (MMARAS) data from 2008 to 2011, this study combines binomial logistic regression and street level analysis that further explores the statistical results and examines other factors that contribute to collisions and increase the potential for serious injury or death in three cities in Metro Manila: Makati, Manila, and Quezon. The results of the binomial regression analysis show that traffic crashes that involve heavy and multiple vehicles, and an elderly pedestrian (60 years old and above), as well as those that occurred during the evening (7 pm to midnight) and late at night (1 am to 5 am) have significantly higher odds of resulting in a fatal outcome; when the crash involves a female pedestrian and when the road surface is wet the odds of a fatal outcome are lower. Moreover, by closely examining the environment of these roadways, the study finds that most pedestrian fatalities occur on high-speed, high-traffic-volume, multilane roadways, that are surrounded by land uses that generate a particularly problematic mix of heavy vehicular and pedestrian traffic. The street level analysis also finds that fatal pedestrian crashes occur close to different types of transit stations. The results of this study of three cities in Metro Manila, reflect the twofold challenge to pedestrian safety in rapidly urbanizing areas in countries such as the Philippines that are classified as lower-middle-income: they face some of the same pedestrian safety issues as more developed areas, but with a much larger number of pedestrians using the streets, and a built environment that was not planned for the high volume and speed of motor vehicle traffic on today’s roadways. Policies and planning that support increased pedestrian safety therefore need to address this dual challenge in the contexts where they are most needed.