Winter westerly disturbances (WWD) are the primary climatic influence within High Mountain Asia during the boreal winter. Here we investigate variations and changes in WWD over the period 1979–2010 and relationships with heavy (85th percentile) precipitation in the Karakoram/western Himalaya (KH) and central Himalaya (CH) using multiple datasets. We show that heavy precipitation events occurring in the KH and CH are often spatiotemporally independent, suggesting differing behavior of WWD affecting each region. The wavelet power spectrum of 200 hPa geopotential height anomalies is used to characterize the frequency and magnitude of individual disturbances and to distinguish synoptic scale variability through time. Our analysis exhibits an enhancement in the strength and frequency of WWD in the KH and indicates an increase in local heavy precipitation events. In contrast, the CH is observed to experience weakening influence of these disturbances and consequently, a decrease in heavy precipitation. Furthermore, we investigate multi-annual variability of WWD and teleconnections with some known modes of climate variability affecting central Asia, including the Arctic Oscillation, Eurasian/Polar Pattern, the El Niño Southern Oscillation, and the Siberian High. Although there is clear evidence that these modes affect circulation and precipitation in High Mountain Asia, their competing influences on WWD are complex and non-linear. These results suggest that a thorough understanding of WWD and their spatiotemporal variations are crucial to improve our knowledge of the hydrologic cycle within High Mountain Asia as well as our ability to project the future status of Asia’s water resources.