Due to climate change, increased regulation of water resources and competition from other beneficial uses, the agricultural sector is under pressure to use water more efficiently. This paper reports the field evaluation of two model-based simulation-optimization approaches for irrigation scheduling: deterministic optimization and stochastic optimization. The field experiments were conducted at the University of California Davis research farm with a processing tomato crop. The crop growth simulation model used in the study was DSSAT-CROPGRO processing tomato. In order to mitigate the impact of weather forecasts inaccuracies, irrigation schedules were updated every 5 to 10 days, depending on operational constraints. These updates were performed via custom graphical user interfaces that enabled the user to visualize the expected outcomes of various decisions or scenarios before choosing which irrigation schedule to implement. An irrigation treatment based on manual monitoring of soil water content with a field-calibrated neutron probe served as benchmark. The model-based treatments achieved yields and water use efficiencies that were not significantly different from those obtained in the neutron probe-based treatment. These results demonstrate the high potential of model-based simulation-optimization approaches for in-season adaptive irrigation scheduling, especially since neutron probes, which are considered one of the most accurate indirect methods of measuring soil water content, are not commonly used by growers.