A quantitative understanding of actual evapotranspiration (ETa) and soil–water dynamics in a hillslope agroecosystem is vital for sustainable water resource management and soil conservation; however, the complexity of processes and conditions involving lateral subsurface flow (LSF) can be a limiting factor in the full comprehension of hillslope soil–water dynamics. The research was carried out at SUPREHILL CZO located on a hillslope agroecosystem (vineyard) over a period of two years (2021–2022) by combining soil characterization and field hydrological measurements, including weighing lysimeters, sensor measurements, and LSF collection system measurements. Lysimeters were placed on the hilltop and the footslope, both having a dynamic controlled bottom boundary, which corresponded to field pressure head measurements, to mimic field soil–water dynamics. Water balance components between the two positions on the slope were compared with the goal of identifying differences that might reveal hydrologically driven differences due to LSF paths across the hillslope. The usually considered limitations of these lysimeters, or the borders preventing LSF through the domain, acted as an aid within this installation setup, as the lack of LSF was compensated for through the pumping system at the footslope. The findings from lysimeters were compared with LSF collection system measurements. Weighing lysimeter data indicated that LSF controlled ETa rates. The results suggest that the onset of LSF contributes to the spatial crop productivity distribution in hillslopes. The present approach may be useful for investigating the impact of LSF on water balance components for similar hillslope sites and crops or other soil surface covers.