An Observing System Simulation Experiment (OSSE) has been defined to assess the potentialities of assimilating winter wheat leaf area index (LAI) estimations derived from remote sensing into the crop growth model WOFOST. Two assimilation strategies are considered: one based on Ensemble Kalman Filter (EnKF) and the second on recalibration/re-initialisation of uncertain model parameters and initial state conditions. The main objective of the OSS Experiment is to estimate the requisites for the remotely sensed LAI, in terms of accuracy and sampling frequency, to reach target of either 25 or 50% reduction of errors on the final estimation of grain yields. Our results demonstrate that EnKF is not suitable for assimilating LAI in WOFOST as the average error on final grain yields estimation globally increases. These poor results can be explained by the possible differences of phenological development existing between assimilated and modelled LAI values (difference called “phenological shift” in our study) which is not corrected by the EnKF-based assimilation strategy. On the contrary, a recalibration-based assimilation approach globally improves the estimation of final grain yields in a significant way. On average, such improvement can reach up to approximately 65% when observations are available all along the growing season. Improvements on the order of 20% can be already be attained early in the season, which is of great interest in a crop yield forecasting perspective. If the first objective (25%) of error reduction on final grain yields can be reached in a quite high number of assimilated LAI observations availabilities and uncertainty levels, the field of possibilities is significantly restricted for the second objective (50%) and implies to have LAI observations available all along the growing season, at least on a weekly basis and with an uncertainty level equal or ideally lower than 10%. These requirements are not currently met from neither a technological nor an operational point of view but the results presented here can provide guidelines for future missions dedicated to crop growth monitoring.