Compound weather and climate extremes have amplified impacts on natural and socioeconomic systems across the world, including Singapore. To better understand the spatial and temporal characteristics of compound climate extremes, including concurrent rainfall and wind speed, as well as dry and hot conditions, we analyzed long-term observations from 11 selected meteorological stations over the period 1985–2020. The results revealed that the north and northeastern parts of Singapore were focal points for both types of compound extremes, with a higher frequency of occurrence than the southwest of the island. Concurrent rainfall and wind speed extremes were the most prominent in December and January thanks to the northeast monsoon, while dry and hot extremes were distributed mainly in the inter-monsoon season, with peaks in March and April. A notable upward trend was also detected for mild and moderate levels of both compound climate extremes over time. According to our review of the impacts, Singapore has benefited from investments in enhanced water infrastructure; water resource availability was less affected; and flash floods were not proportionally related to the severity of climate extremes. The forests in the urban landscape of Singapore also exhibit resilience to drought.