Dental disorders are a serious health problem in equine medicine, their early recognition benefits the long-term general health of the horse. Most of the initial signs of Equine Odontoclastic Tooth Resorption and Hypercementosis (EOTRH) syndrome concern the alveolar aspect of the teeth, thus, the need for early recognition radiographic imaging. This study is aimed to evaluate the applicability of entropy measures to quantify the radiological signs of tooth resorption and hypercementosis as well as to enhance radiographic image quality in order to facilitate the identification of the signs of EOTRH syndrome. A detailed examination of the oral cavity was performed in eighty horses. Each evaluated incisor tooth was assigned to one of four grade–related EOTRH groups (0–3). Radiographs of the incisor teeth were taken and digitally processed. For each radiograph, two–dimensional sample (SampEn2D), fuzzy (FuzzEn2D), permutation (PermEn2D), dispersion (DispEn2D), and distribution (DistEn2D) entropies were measured after image filtering was performed using Normalize, Median, and LaplacianSharpening filters. Moreover, the similarities between entropy measures and selected Gray–Level Co–occurrence Matrix (GLCM) texture features were investigated. Among the 15 returned measures, DistEn2D was EOTRH grade–related. Moreover, DistEn2D extracted after Normalize filtering was the most informative. The EOTRH grade–related similarity between DistEn2D and Difference Entropy (GLCM) confirms the higher irregularity and complexity of incisor teeth radiographs in advanced EOTRH syndrome, demonstrating the greatest sensitivity (0.50) and specificity (0.95) of EOTRH 3 group detection. An application of DistEn2D to Normalize filtered incisor teeth radiographs enables the identification of the radiological signs of advanced EOTRH with higher accuracy than the previously used entropy–related GLCM texture features.