Woody plant encroachment and subsequent thicketization is a global phenomenon that has been demonstrated to reduce groundwater recharge, yet it is unknown whether reducing woody plant cover will restore groundwater recharge rates to pre-encroachment levels. We investigated how savanna restoration influences soil moisture dynamics and deep drainage in the Post Oak Savanna ecoregion of Texas, USA, which overlies the recharge zone of the underlying Carrizo–Wilcox Aquifer. We compared soil moisture and deep drainage responses in water years 2023 and 2024 across the following three vegetation states: restored savanna, woodland mosaic and thicketized woodland. We found that savanna had higher profile mean volumetric water content than both woodland mosaic and thicketized woodland. Deep drainage rates were consistently higher in the savanna than in the woodland mosaic, and those in the intercanopy area were higher than those in the undercanopy areas. A water balance analysis provided independent validation of the matric potential based drainage estimates, demonstrating consistent temporal patterns and overlapping ranges. These findings indicate the effectiveness of thicketized savanna restoration in enhancing deep drainage and sustaining groundwater resources in subhumid landscapes.