In Europe, most of vineyards are managed under rainfed conditions, where water deficit has become increasingly an issue. The flowering-veraison phenophase represents an important period for vine response to water stress, which is known to depend on variety characteristics, soil and climate conditions. In this paper, we have carried out a retrospective analysis for important European wine regions over 1986–2015, with objectives to assess the mean Crop Water Stress Indicator (CWSI) during flowering-veraison phase, and potential Yield Lose Rate (YLR) due to seasonal cumulative water stress. Moreover, we also investigate if advanced flowering-veraison phase can lead to alleviated CWSI under recent-past conditions, thus contributing to reduced YLR. A process-based grapevine model is employed, which has been extensively calibrated for simulating both flowering and veraison stages using location-specific observations representing 10 different varieties. Subsequently, grid-based modelling is implemented with gridded climate and soil datasets and calibrated phenology parameters. The findings suggest wine regions with higher mean CWSI of flowering-veraison phase tend to have higher potential YLR. However, contrasting patterns are found between wine regions in France-Germany-Luxembourg and Italy-Portugal-Spain. The former tends to have slight-to-moderate drought conditions (CWSI<0.5) along with a negligible-to-moderate YLR (<30%), whereas the latter is found to have severe-to-extreme drought (CWSI>0.5) and substantial YLR (>40%). Wine regions prone to a high drought risk (CWSI>0.75) are also identified, which are concentrated in southern Mediterranean Europe. Advanced flowering-veraison phase over 1986–2015, could have benefited from more spring precipitation and cooler temperatures for wine regions of Italy-Portugal-Spain, leading to reduced mean CWSI and YLR. For those of France-Germany-Luxembourg, this can have reduced flowering-veraison precipitation, but prevalent reductions of YLR are also found, possibly due to shifted phase towards a cooler growing-season with reduced evaporative demands. Our study demonstrates flowering-verasion water deficit is critical for potential yield, which can have different impacts between Central and Southern European wine regions. This phase can be advanced under a warmer climate, thus having important implications for European rainfed vineyards. The overall outcome may provide new insights for appropriate viticultural management of seasonal water deficits under climate change.