Monitoring within-field crop variability at fine spatial and temporal resolution can assist farmers in making reliable decisions during their agricultural management; however, it traditionally involves a labor-intensive and time-consuming pointwise manual process. To the best of our knowledge, few studies conducted a comparison of Sentinel-2 with UAV data for crop monitoring in the context of precision agriculture. Therefore, prospects of crop monitoring for characterizing biophysical plant parameters and leaf nitrogen of wheat and barley crops were evaluated from a more practical viewpoint closer to agricultural routines. Multispectral UAV and Sentinel-2 imagery was collected over three dates in the season and compared with reference data collected at 20 sample points for plant leaf nitrogen (N), maximum plant height, mean plant height, leaf area index (LAI), and fresh biomass. Higher correlations of UAV data to the agronomic parameters were found on average than with Sentinel-2 data with a percentage increase of 6.3% for wheat and 22.2% for barley. In this regard, VIs calculated from spectral bands in the visible part performed worse for Sentinel-2 than for the UAV data. In addition, large-scale patterns, formed by the influence of an old riverbed on plant growth, were recognizable even in the Sentinel-2 imagery despite its much lower spatial resolution. Interestingly, also smaller features, such as the tramlines from controlled traffic farming (CTF), had an influence on the Sentinel-2 data and showed a systematic pattern that affected even semivariogram calculation. In conclusion, Sentinel-2 imagery is able to capture the same large-scale pattern as can be derived from the higher detailed UAV imagery; however, it is at the same time influenced by management-driven features such as tramlines, which cannot be accurately georeferenced. In consequence, agronomic parameters were better correlated with UAV than with Sentinel-2 data. Crop growers as well as data providers from remote sensing services may take advantage of this knowledge and we recommend the use of UAV data as it gives additional information about management-driven features. For future perspective, we would advise fusing UAV with Sentinel-2 imagery taken early in the season as it can integrate the effect of agricultural management in the subsequent absence of high spatial resolution data to help improve crop monitoring for the farmer and to reduce costs.