Improvements to agricultural water and crop managements require detailed information on crop and soil states, and their evolution. Data assimilation provides an attractive way of obtaining these information by integrating measurements with model in a sequential manner. However, data assimilation for soil-water-atmosphere-plant (SWAP) system is still lack of comprehensive exploration due to a large number of variables and parameters in the system. In this study, simultaneous state-parameter estimation using ensemble Kalman filter (EnKF) was employed to evaluate the data assimilation performance and provide advice on measurement design for SWAP system. The results demonstrated that a proper selection of state vector is critical to effective data assimilation. Especially, updating the development stage was able to avoid the negative effect of “phenological shift”, which was caused by the contrasted phenological stage in different ensemble members. Simultaneous state-parameter estimation (SSPE) assimilation strategy outperformed updating-state-only (USO) assimilation strategy because of its ability to alleviate the inconsistency between model variables and parameters. However, the performance of SSPE assimilation strategy could deteriorate with an increasing number of uncertain parameters as a result of soil stratification and limited knowledge on crop parameters. In addition to the most easily available surface soil moisture (SSM) and leaf area index (LAI) measurements, deep soil moisture, grain yield or other auxiliary data were required to provide sufficient constraints on parameter estimation and to assure the data assimilation performance. This study provides an insight into the response of soil moisture and grain yield to data assimilation in SWAP system and is helpful for soil moisture movement and crop growth modeling and measurement design in practice.