Keratoconus (KC) is the most common corneal ectasia characterized by progressive corneal thinning, protrusion, and irregular astigmatism. The Amsler–Krumeich classification based on the analysis of corneal topography, corneal thickness, refraction and biomicroscopy is the most commonly used; recently, a new classification based on anterior segment Optical Coherence Tomography was introduced by Sandali and colleagues. Since there is no information about the possible agreement between these two classifications, the aim of this study is to compare the stratification of consecutive KC patients using the Amsler–Krumeich and Sandali classifications, and to further ascertain KC cases in which one classification is preferred over the other. Overall, 252 eyes of 137 patients (41.45 ± 16.93 years) were analyzed: in 156 eyes (61.9%), the Amsler and Sandali staging differed in one stage while in 75 cases (29.8%) it differed in two or more stages. In 222 eyes (88.1%), the Sandali staging was higher compared to the Amsler one. These results show that the two classifications are not fully interchangeable: the Amsler–Krumeich classification is more appropriate in identifying and longitudinally monitoring patients with early stages of KC, while the Sandali classification for the diagnosis and follow-up of patients with more advanced stages, particularly when a surgical planning has to be chosen.