This study investigates the chemical composition and sensory properties of wines from Cabernet Sauvignon vines grown under controlled water deficit in two consecutive seasons. The wines were made from fruit of grapevines that were maintained under three water status levels (i.e. T1, Ψstem = −0.8 MPa; T2, Ψstem = −0.9 MPa; T3, Ψstem = −1.0 MPa) from veraison until harvest. Our results suggest that wine phenolic composition was affected by controlled water deficit, where T3 wines exhibited a higher concentration of total phenols, total anthocyanins and chroma (C*) in both seasons. These results coincide with the principal component analysis that indicated a substantial separation between years and deficit irrigation. We found that irrigation treatments only produce differences in concentration, but not in anthocyanin composition in both years. Separation of proanthocyanidins fractions by solid phase extraction using Sep-Pak Plus tC18 cartridges showed only a change in the concentration of the monomeric fraction in 2014 season, but not in the proportion of the different proanthocyanidins fractions in both seasons. Finally, the sensory composition of wines showed differences that depend on the season and resulted in more red fruits, more fullness perception in mouth and more color intensity in wines from less irrigated treatments.