Permeable pavement (PP) is one of the widely adopted low-impact development measures in construction for enhancing urban water retention capacity, which has received increasing attention. To assess the performance of PP in surface runoff management, a comprehensive study involving hydrological monitoring and simulation was conducted at a site in Taipei. In the hydrological monitoring phase, data from 41 effective rainfall events were collected, providing a robust dataset for the analysis of PP effects. Subsequently, six distinct PP implementations and four varied rainfall scenarios were meticulously designed and simulated using the Storm Water Management Model (SWMM). The results showed that (1) PP implementation contributes to mitigating surface runoff in the study site. The observed reduction in surface runoff spans a significant range, from 5–30.8%, with an average runoff reduction rate of approximately 14.6% for each effective rainfall event. (2) With an increasing rainfall return period, the percentage reduction of total and peak runoff decreases. The marginal control on both total and peak runoff decreased with increasing levels of PP implementation. (3) PP measures in reducing peak runoff flow and the time of arrival of peak runoff flow were relatively weak. (4) A new indicator was defined to characterize the cost-effectiveness of project construction, which helps in project management.