The current study investigated hydroclimatic extremes in Vhembe, Lejweleputswa, and uMgungundlovu District Municipalities based on streamflow data from 21 river gauge stations distributed across the study site for the period spanning 1985–2023. Statistical metrics such as the annual mean and maximum streamflow, as well as trends in annual, maximum, seasonal, and high/low flow, were used to evaluate the historical features of streamflow in each of the three district municipalities. Moreover, the Standardized Streamflow Index (SSI) time series computed from streamflow observations at 3- and 6-month accumulation periods were used to assess hydroclimatic extremes, including drought episodes, proportion of wet/dry years and trends in SSI, drought duration (DD), and drought severity (DS). The results indicate that the three district municipalities have experienced localized and varying degrees of streamflow levels and drought conditions. The uMgungundlovu District Municipality in particular has experienced a significant decline in annual and seasonal streamflow as well as an increase in drought conditions during the 38-year period of analysis. This is supported by the negative trends observed in most of the assessed metrics (e.g., annual, maximum, seasonal, low/high flow, and SSI), whereas DD and DS showed positive trends in all the stations, suggesting an increase in prolonged duration and severity of drought. The Lejweleputswa District Municipality depicted positive trends in most of the assessed metrics, suggesting that streamflow increased, whereas drought decreased in the region over the 38-year period of study. Moreover, the Vhembe District Municipality experienced both negative and positive trends, suggesting localized variations in dry and wet conditions. The results presented in this study contribute towards drought monitoring and management efforts in support of policy- and decision-making that aim to uplift water resources management and planning at local and district municipality levels.