In this study, the transport and fate of nitrate within the soil profile and nitrate leaching to drains were analyzed by comparing historic field data with the simulation results of the DRAINMOD model. The nitrogen version of DRAINMOD was used to simulate the performance of the nitrogen transport and transformation of the Hooibeekhoeve experiment, situated in the sandy region of the Kempen (Belgium) and conducted for a 30-year (1969–1998) period. In the analysis, a continuous cropping with maize was assumed. Comparisons between experimentally measured and simulated state variables indicate that the nitrate concentrations in the soil and nitrate leaching to drains are controlled by the fertilizer practice, the initial conditions, and the rainfall depth and distribution. Furthermore, the study reveals that the model used gives a fair description of the nitrogen dynamics in the soil and subsurface drainage at field scale. From the comparative analysis between experimental data and simulation results it can also be concluded that the model after calibration is a useful tool to optimize as a function of the combination “climate-crop-soil-bottom boundary condition” the nitrogen application strategy resulting in an acceptable level of nitrate leaching for the environment.