One of the most ubiquitous and detrimental types of environmental contamination in the world is crude oil pollution. When released into either the aquatic or terrestrial environments, this pollution can negatively impact flora and fauna, as well as human health. Hence, a rapid and affordable spatial assessment of the pollution is favored to limit the spill’s effects. Using airborne hyperspectral remote sensing (HRS) for crude oil detection in terrestrial areas has been investigated in previous studies, which mainly relied on heavily oiled artificial samples. These studies and others based their methodologies on the premise that the spectral features of petroleum hydrocarbon (PHC) are clearly observable, which might not be true in all cases. In this study, we aimed at assessing the true potential of using HRS for terrestrial oil spill mapping in a real disaster site in southern Israel, where laboratory and controlled conditions do not apply. Using the AISA SPECIM Fenix1 K sensor, we collected airborne image of the study site and analyzed the data with advanced data mining techniques. Various challenges and limitations arose from the airborne HRS image being taken two and a half years after the crude oil had been released into the environment and exposed to the surface. Here, no spectral features of PHC were detectable in the spectrum, preventing the use of PHC indices and spectral methods developed by others. Nevertheless, by using standardization techniques, vicarious band selection, dimension reduction, multivariate calibration, and supervised machine-learning, we were able to successfully distinguish between contaminated pixels from non-contaminated ones. Classification accuracy metrics of overall accuracy, sensitivity, specificity, and Kappa yielded good results of 0.95, 0.95, 0.95 and 0.9, respectively, for cross-validation, and 0.93, 0.91, 0.94 and 0.85, for the validation dataset. Classified image and test scenes also showed strong agreement with an orthophoto image taken several days after the disaster, when the pollution was clearly visible. Thus, we conclude that HRS technology can detect PHC traces in an oil spill site, even under the most challenging conditions.