The Sava River Basin (SRB) extends across six countries (Slovenia, Croatia, Bosnia and Herzegovina, Serbia, Albania, and Montenegro) and is a major tributary of the Danube River (DR). The Sava River (SR) originates in the alpine region of Slovenia, and, in support of a Slovenian government initiative to increase clean, sustainable energy, multiple hydropower facilities have been constructed within the past ~20 years. Given the importance of this river system for varying demands, including energy production, information about past (paleo) drought and pluvial periods would provide important information to water managers and planners. Seasonal (April–May–June–July–August–September—AMJJAS) streamflow data were obtained for two SRB gauges (Jesenice and Catez) in Slovenia. The Jesenice gauge is in the extreme headwaters of the SR, upstream of any major water control structures, and is considered an unimpaired (minimal anthropogenic influence) gauge. The Catez gauge is located on the SR near the Slovenia–Croatia border, thus providing an estimate of streamflow leaving Slovenia (entering Croatia). The Old World Drought Atlas (OWDA) provides an annual June–July–August (JJA) self-calibrating Palmer Drought Severity Index (scPDSI) derived from 106 tree-ring chronologies for 5414 grid points across Europe from 0 to 2012 AD. In lieu of tree-ring chronologies, this dataset was used as a proxy to reconstruct (for ~2000 years) seasonal streamflow. Prescreening methods included the correlation and temporal stability of seasonal streamflow and scPDSI cells. The retained scPDSI cells were then used as predictors (independent variables) to reconstruct streamflow (predictive and/or dependent variables) in regression-based models. This resulted in highly skillful reconstructions of SRB seasonal streamflow from 0 to 2012 AD. The reconstructions were evaluated, and both low flow (i.e., drought) and high flow (i.e., pluvial) periods were identified for various filters (5-year to 30-year). When evaluating the most recent ~20 years (2000 to present), multiple low-flow (drought) periods were identified. For various filters (5-year to 15-year), the 2003 end-year consistently ranked as one of the lowest periods, while the 21-year period ending in 2012 was the lowest flow period in the ~2000-year reconstructed-observed-historic period of record. The ~30-year period ending in 2020 was the lowest flow period since the early 6th century. A decrease in pluvial (wet) periods was identified in the observed-historic record when compared to the paleo record, again confirming an apparent decline in streamflow. Given the increased activities (construction of water control structures) impacting the Sava River, the results provide important information to water managers and planners.