A research study was conducted in an open field tomato crop in order to: (i) Evaluate the capability of Sentinel-2 imagery to assess tomato canopy growth and its crop water requirements; and (ii) explore the possibility to predict crop water requirements by assimilating the canopy cover estimated by Sentinel-2 imagery into AquaCrop model. The pilot area was in Campania, a region in the south west of Italy, characterized by a typical Mediterranean climate, where field campaigns were conducted in seasons 2017 and 2018 on processing tomato. Crop water use and irrigation requirement were estimated by means of three different methods: (i) The AquaCrop model; (ii) an irrigation advisory service based on Sentinel-2 imagery known as IRRISAT and (iii) assimilating the canopy cover estimated by Sentinel-2 imagery into AquaCrop model Sentinel-2 imagery proved to be effective for monitoring canopy growth and for predicting irrigation water requirements during mid-season stage of the crop, when the canopy is fully developed. Conversely, the integration of the Sentinel-2 imagery with a crop growth model can contribute to improve the irrigation water requirement predictions in the early and development stage of the crop, when the soil evaporation is not negligible with respect to the total evapotranspiration.