Introduction: Pedestrians at high-speed midblock crossings with the intention to cross the road usually face safety risks due to difficulty in judging the available gaps. The risk to pedestrians is high in developing nations like India since priorities are not respected by road users. Moreover, the non-yielding vehicular traffic puts pedestrians at further risk. While crossing the road, pedestrians are clear about rejecting small gaps and accepting the large gaps, however, they experience a dilemma between the small and large gaps. Method: This study attempts to model the dilemma zone for pedestrians intending to cross the high-speed roads (posted speed limit of 60 km/h). The field data were collected using high-definition video cameras at two uncontrolled midblock crossings, each in the cities of Mumbai and Kolhapur, located in the southwestern part of India. The variations in the spatial gap acceptance behavior were analyzed for 1,107 pedestrian observations using binary logit models. Results: The findings revealed that the length and the distribution of the dilemma zone were significantly affected by the speed of the approaching vehicle and the distance from it. Moreover, the influence of vehicle type (truck, car, or two-wheeler), pedestrian type (walking alone or in a group), crossing speed, and waiting time also influenced pedestrians’ gap acceptance behavior. Interestingly, pedestrians’ gender did not play a significant role in their road crossing decisions. Conclusions: Overall, the study identified the dilemma zone boundaries that will help pedestrians to judge the safe gaps while crossing, and in turn, reduce the probability of pedestrian-vehicle crashes. Practical Application: The proposed dilemma zone intends to protect the pedestrians by assisting in making precise crossing decisions at high-speed midblock crossings.