AbstractThe increasing concern over agricultural practices' impact on groundwater quality necessitates comprehensive studies to evaluate and compare monitoring strategies for nitrate leaching. This work addresses this imperative by examining three methodologies: deep vadose‐zone monitoring, shallow groundwater intensive monitoring, and field‐level mass balance. The primary objective of the study was to assess nitrate leaching from an intensively cropped processing tomato rotation field using three different methods. Additionally, this study focuses on contrasting conditions between the growing season (characterized by drought in some years) and the winter/rainy season (characterized by extreme precipitation in some years). Results indicate varying degrees of nitrate leaching across methods, with all approaches detecting leaching events during the growing season and off‐season precipitation. Despite uncertainties inherent in field‐level mass balance estimates, they align reasonably with intensive in‐situ monitoring results using the deep Vadose Monitoring System (VMS). Throughout two growing seasons and corresponding fall‐winter rainy periods, the VMS effectively tracked seasonal nitrogen leaching below the root zone, correlating with observed groundwater nitrate concentrations increases following extreme precipitation events. Nitrate leaching increased during heavy rainfall in the winter following dry summer periods observed across the deep vadose zone using two VMS systems. This underscores the importance of continuous monitoring and assessment in understanding nitrate dynamics and groundwater contamination risks. In conclusion, this study contributes to knowledge and ongoing research by providing insights into effective monitoring strategies for nitrate leaching into groundwater from intensive cropping systems.