Soil hydrological conditions influence crop growth and groundwater recharge and, thus, precise knowledge of such conditions at field scale is important for the investigation of agricultural systems. In our study, we analyzed soil hydrological conditions at three agricultural experimental field plots with sandy soils and different crop rotations using a 22-year period from 1993 to 2014 with daily volumetric soil water contents measured by the Time Domain Reflectometry with Intelligent MicroElements (TRIME)-method and pressure heads determined by automatic recording tensiometers. These measured data were compared with soil water contents and pressure heads simulated by a process-based agroecosystem model. Within this 22-year period, time spans with a better model performance and periods with a lower goodness of fit between simulations and observations were observed. The lower goodness of fit in the summer periods was attributed to inadequate calculations of root water uptake. Measurement errors of the TRIME-probes and differences between soil water contents measured by TRIME and pressure heads observed by tensiometers due to different measurement volumes, precision and measuring principles were identified as further reasons for mismatches between simulated and measured model outputs.