The use of exogenous organic matter (EOM) fertilizers, such as digestate and cattle slurry, has gained increasing attention due to their potential to reduce reliance on synthetic fertilizers in agriculture. This study evaluated the utility of Sentinel-2 imagery for monitoring different liquid EOM fertilizers applied on winter wheat crop, using both proximal and satellite scales. At the proximal scale, spectral field measurements were taken of experimental fields consisting of three treatments (cattle slurry, liquid and raw digestates) and a control over 46 days. Field reflectance spectra were simulated into the MSI spectral bands of Sentinel-2. At the satellite scale, Sentinel-2 images were analyzed before and after EOM application for each experimental field. EOM and vegetation indices were used to monitor EOM application at both scales. The main findings of this study refer to digestates. Firstly, the spread of digestates on emerging wheat can be easily detected in late winter, up to 15 days after application. Secondly, the visible to near infrared bands are the most impacted the first days after spreading and the visible to red-edge bands are persistently impacted 15 days after spreading. Finally, the detection of spring spreading events is constrained or even hindered by developed vegetation. These findings did not apply to cattle slurry, which was hardly visible in the field and in Sentinel-2 images. This Sentinel-2-based approach can serve as a primer for further implementation over larger fields.