Floods are among the most severe consequences of climate change, causing significant damage across several sectors, including agriculture. Nevertheless, the assessment of agricultural flood damage remains limited, particularly in agriculturally intensive regions where timely support is crucial. This work proposes a data-driven approach for assessing crop flood damage through a machine learning classification framework applied to features derived from Earth Observation (EO) data, trained and tested on field-level damage data collected by agronomists. Specifically, we applied a Random Forest model to classify fields into three damage classes by integrating Sentinel-2–derived indices, topographic information, and flood extent maps. The analysis focused on the flood event that struck the Emilia-Romagna region (Italy) in May 2023, one of the costliest floods globally that year. The model was trained and tested on 412 fields, achieving an overall accuracy of 0.74, with precision, recall, and F1 score of 0.75, 0.74, and 0.74, each with a standard deviation of 0.04, indicating stable model performance. The model accurately identified high-damage fields, which were characterized by greater flood exposure, lower elevations, and pronounced declines in vegetation indices. However, it struggled to distinguish between no-damage and medium-damage fields, particularly for permanent crops, where damage often occurs beneath the canopy and flooded areas may be partially occluded. The main novelty of this work lies in the use of in situ crop damage assessments, enabling a data-driven estimation of flood impacts. These results have direct implications for policymakers: the framework relies on free EO data, providing a tool that can support post-event compensation and decision-making in flood-prone regions.