The influence of controlled water deficit on the phenolic composition and gene expression of VvLAR2, VvMYBPA1, VvMYBPA2 and VvMYB4a in Cabernet Sauvignon grape skins throughout ripening was investigated. The assay was carried out on own-rooted Vitis vinifera plants cv. Cabernet Sauvignon in a commercial vineyard from veraison until commercial harvest. Three irrigation regimes were used from veraison until harvest with the following treatments: T1: 3.6 mm day-1; T2: 1.8 mm day-1 and T3: 0.3 mm day-1. The content of total phenols and total anthocyanins in grape skins increased during ripening, but water deficit did not produce differences among treatments in the total anthocyanin concentration. Proanthocyanidins (PAs) decreased throughout ripening, although approximately 25 days after veraison (DAV), their content slightly increased. This effect was more pronounced in the most restrictive treatment (T3). A similar pattern was observed in the transcript abundance of VvLAR2, VvMYBPA1 and VvMYB4a. PAs separation revealed differences in concentration but not in the proportion among fractions among the irrigation treatments. Additionally, controlled water deficit increased the mean degree of polymerization and the flavan-3-ol polymeric concentration in grape skins throughout ripening but with no effects on the extent of PAs galloylation. Our results suggest that the water status of Cabernet Sauvignon grapevines affects the gene expression for proteins involved in the synthesis of PAs, increasing their concentration and also their composition, with further evidence for the efficacy of a convenient, controlled water deficit strategy for grapevine cultivation.