Remote sensing data play a crucial role in monitoring crop dynamics in the context of precision agriculture by characterizing the spatial and temporal variability of crop traits. At present there is special interest in assessing the long-term impacts of biochar in agro-ecosystems. Despite the growing body of literature on monitoring the potential biochar effects on harvested crop yield and aboveground productivity, studies focusing on the detailed crop performance as a consequence of long-term biochar enrichment are still lacking. The primary objective of this research was to evaluate crop performance based on high-resolution unmanned aerial vehicle (UAV) imagery considering both crop growth and health through RGB and multispectral analysis, respectively. More specifically, this approach allowed monitoring of century-old biochar impacts on winter wheat crop performance. Seven Red-Green-Blue (RGB) and six multispectral flights were executed over 11 century-old biochar patches of a cultivated field. UAV-based RGB imagery exhibited a significant positive impact of century-old biochar on the evolution of winter wheat canopy cover (p-value = 0.00007). Multispectral optimized soil adjusted vegetation index indicated a better crop development over the century-old biochar plots at the beginning of the season (p-values < 0.01), while there was no impact towards the end of the season. Plant height, derived from the RGB imagery, was slightly higher for century-old biochar plots. Crop health maps were computed based on principal component analysis and k-means clustering. To our knowledge, this is the first attempt to quantify century-old biochar effects on crop performance during the entire growing period using remotely sensed data. Ground-based measurements illustrated a significant positive impact of century-old biochar on crop growth stages (p-value of 0.01265), whereas the harvested crop yield was not affected. Multispectral simplified canopy chlorophyll content index and normalized difference red edge index were found to be good linear estimators of harvested crop yield (p-value(Kendall) of 0.001 and 0.0008, respectively). The present research highlights that other factors (e.g., inherent pedological variations) are of higher importance than the presence of century-old biochar in determining crop health and yield variability.