In early 2018, Cape Town (population ~3.7 million) was at risk of being one of the first major metropolitan areas in the world to run out of water. This was due to a severe multi-year drought that led to the levels of supply dams falling to an unprecedented low. Here we analyze rainfall data from the city catchment areas, including rare centennial records from the surrounding region, to assess the severity of the 2015–2017 drought. We find that there has been a long-term decline in the number of winter rainfall days, but this trend has been generally masked by fluctuations in rainfall intensity. The recent drought is unprecedented in the centennial record and represents a combination of the long-term decline in rainfall days and a more recent decline in rainfall intensity. Cold fronts during the winter months are responsible for most of the rainfall reaching Cape Town and our analysis shows no robust regional trend in the number of fronts over the last 40 years. Rather, the observed multidecadal decline in rainfall days, which threatens to increase the occurrence of severe drought, appears to be linked to a decrease in the duration of rainfall events associated with cold fronts. This change in rainfall characteristics associated with fronts appears to be linked to Hadley Cell expansion seen across the Southern Hemisphere and an increasing trend in post-frontal high-pressure conditions that suppress orographically enhanced rainfall.