The timely and accurate estimation of soil water content (SWC) and evapotranspiration (ET) is of great significance in drought estimation, irrigation management, and water resources comprehensive utilization. The unsupervised classification was used to identify the crops in the region. Based on MOD16A2 and the meteorological data, a SEBS model was used to estimate the ET in the Jiefangzha Irrigation Field from 2011 to 2015. Based on the crop water stress index (CWSI), the SWC in 2014 was retrieved and verified with the measured SWC on different underlying surfaces (sunflower, corn, wheat, and pepper). The results showed that: (1) The positional accuracy of maize, sunflower, wheat, and pepper are 0.81, 0.80, 0.90, and 0.82, respectively; (2) The annual ET from 2011 to 2015 presented well the spatial distribution of the ET within the field; (3) The validation results of the estimated SWC on the underlying surface of wheat and sunflower showed a good robustness, the R2 was 0.748 and 0.357, respectively, the RMSE was 2.61% and 2.309%, respectively, and the MAE was 2.249% and 1.975%, respectively. However, for maize and pepper with more irrigation times, the SWC estimation results, based on the CWSI were poor, indicating that the method was more sensitive to soil drought and suitable for the crop SWC estimation with less irrigation and drought tolerance. The results can provide a reference for the agricultural water resources management and the irrigation forecast at a regional scale.