Study region: The study region is represented by seven irrigation districts distributed under different climate and topography conditions in Italy. Study focus: This study explores the reliability and consistency of the global ERA5 single levels and ERA5-Land reanalysis datasets in predicting the main agrometeorological estimates commonly used for crop water requirements calculation. In particular, the reanalysis data was compared, variable-by-variable (e.g., solar radiation, R; air temperature, T; relative humidity, RH; wind speed, u; reference evapotranspiration, ET), with in situ agrometeorological observations obtained from 66 automatic weather stations (2008–2020). In addition, the presence of a climate-dependency on their accuracy was assessed at the different irrigation districts. New hydrological insights for the region: A general good agreement was obtained between observed and reanalysis agrometeorological variables at both daily and seasonal scales. The best performance was obtained for T, followed by RH, R, and u for both reanalysis datasets, especially under temperate climate conditions. These performances were translated into slightly higher accuracy of ET estimates by ERA5-Land product, confirming the potential of using reanalysis datasets as an alternative data source for retrieving the ET and overcoming the unavailability of observed agrometeorological data.