In dengue-endemic areas, transmission shows both a seasonal and interannual variability. To investigate how rainfall impacts dengue seasonality in Singapore, we carried out a longitudinal survey in the Geylang neighborhood from August 2014 to August 2015. The survey comprised of twice-weekly random inspections to outdoor breeding habitats and continuous monitoring for positive ones. In addition, observations of rainstorms were collected. Out of 6824 inspected habitats, 67 contained Aedes aegypti, 11 contained Aedes albopictus and 24 contained Culex spp. The main outdoors habitat of Aedes aegypti was storm drains (54/67). We found that 80% of breeding sites in drains (43/54) were lost after intense rainstorms related to the wet phase of the Northeast monsoon (NE) between November 2014 and early January 2015. Subsequently, 95% (41/43) of these flushed drains had dried out during the dry phase of the NE in late January-February 2015. A return in the outdoor breeding of Aedes aegypti was observed after the onset of Southwest monsoon (SW) between May and August 2015. There was also a reduction in productivity of breeding habitats for larvae and pupae after the onset of the NE. In wet equatorial regions like Singapore, rainfall varies with the monsoons. A monsoon-driven sequence of flushing and drying shapes the outdoor seasonal abundance of Aedes aegypti. This finding can be used to optimize vector control strategies and better understand dengue in the context of climate change.