Agricultural water use represents more than 70% of the world’s freshwater through irrigation water inputs that are poorly known at the field scale. Irrigation monitoring is thus an important issue for optimizing water use in particular with regards to the water scarcity that the semi-arid regions are already facing. In this context, the aim of this study is to develop and evaluate a new approach to predict seasonal to daily irrigation timing and amounts at the field scale. The method is based on surface soil moisture (SSM) data assimilated into a simple land surface (FAO-56) model through a particle filter technique based on an ensemble of irrigation scenarios. The approach is implemented in three steps. First, synthetic experiments are designed to assess the impact of the frequency of observation, the errors on SSM and the a priori constraints on the irrigation scenarios for different irrigation techniques (flooding and drip). In a second step, the method is evaluated using in situ SSM measurements with different revisit times (3, 6 and 12 days) to mimic the available SSM product derived from remote sensing observation. Finally, SSM estimates from Sentinel-1 are used. Data are collected on different wheat fields grown in Morocco, for both flood and drip irrigation techniques in addition to rainfed fields used for an indirect evaluation of the method performance. Using in situ data, accurate results are obtained. With an observation every 6 days to mimic the Sentinel-1 revisit time, the seasonal amounts are retrieved with R > 0.98, RMSE < 32 mm and bias < 2.5 mm. Likewise, a good agreement is observed at the daily scale for flood irrigation as more than 70% of the detected irrigation events have a time difference from actual irrigation events shorter than 4 days. Over the drip irrigated fields, the statistical metrics are R = 0.74, RMSE = 24.8 mm and bias = 2.3 mm for irrigation amounts cumulated over 15 days. When using SSM products derived from Sentinel-1 data, the statistical metrics on 15-day cumulated amounts slightly dropped to R = 0.64, RMSE = 28.7 mm and bias = 1.9 mm. The metrics on the seasonal amount retrievals are close to assimilating in situ observations with R = 0.99, RMSE = 33.5 mm and bias = −18.8 mm. Finally, among four rainfed seasons, only one false event was detected. This study opens perspectives for the regional retrieval of irrigation amounts and timing at the field scale and for mapping irrigated/non irrigated areas.