The increasing number of pluvial floods due to extreme climatic events or poor maintenance of the drainage networks urge for assessing the performance of the urban drainage system (UDS). This paper presents a comprehensive evaluation of the UDS of Gurugram City, India. While the limited availability of sub-hourly precipitation and finer resolution geospatial data pose major challenges in the detailed analyses through Storm Water Management Model (SWMM), it was circumvented by utilizing the high-resolution remotely sensed datasets viz., IMERG (half-hourly precipitation data from 2000 to 2019), ALOS PALSAR (Digital Elevation Model) and Sentinel-2 (land use/land cover). Functional failure scenarios (i.e., the combinations of climate change and urbanization) were simulated to assess the impacts on the resilience of the UDS. The modelling results showed that individually, climate change would impose a more serious threat than urbanization, whereas their combinations would significantly hamper the resilience of the UDS. The structural failure (only single link-failure) scenarios were analyzed, and 11 out of 25 conduits were identified to be non-resilient. The study highlights the importance of the readily available remote sensing datasets, which fill the gap of non-availability of ground-based datasets at desirable resolutions, especially in developing countries.