Abstract In southwestern Ontario, rain-fed crop production frequently fails to achieve its yield potential because of growing-season droughts and/or uneven rainfall distribution. The objective of this study was to determine if the Decision Support System for Agrotechnology Transfer (DSSAT) v4.5 model could adequately simulate corn and soybean yields, near-surface soil water contents, and cumulative nitrate-N losses associated with regular free tile drainage (TD) and controlled tile drainage with optional subsurface irrigation (CDS). The simulations were compared to observations collected between 2000 and 2004 from both TD and CDS field experiments on a Perth clay loam soil at the Essex Region Conservation Authority demonstration farm, Holiday Beach, Ontario, Canada. There was good model-data agreement for crop yields, near-surface (0–30 cm) soil water content and cumulative annual tile nitrate-N loss in both the calibration and validation years. For both TD and CDS, the CENTURY soil C/N model in DSSAT simulated water content and cumulative tile nitrate-N loss with normalized root mean square error (n-RMSE) values ranging from 9.9 to 14.8% and 17.8 to 25.2%, respectively. The CERES-Maize and CROPGRO-Soybean crop system models in the DSSAT simulated corn and soybean yields with n-RMSE values ranging from 4.3 to 14.0%. It was concluded that the DSSAT v4.5 model can be a useful tool for simulating near-surface soil water content, cumulative tile nitrate-N losses, and corn and soybean yields associated with CDS and TD water management systems.