Drought stress has a profound impact on grapevine productivity and significantly alters key quality-related traits of berries. Although research has been conducted on the effects of individual drought events, there is still a knowledge gap regarding the cumulative consequences of repeated exposure to water scarcity and the influence of the timing of stress imposition. To address this gap, a field experiment was conducted to investigate the impacts of repeated drought stress on yield, berry composition, and the phenolic profile of grape berries. The results indicate that yield is primarily influenced by pre-veraison water deficit. Although the number of clusters was only slightly reduced, a substantial decrease in berry size was observed, resulting in a notable reduction in overall yield.