Date palm (Phoenix dactylifera L.) fruit samples belonging to the ‘Mejhoul’ and ‘Boufeggous’ cultivars were harvested at the Tamar stage and used in our experiments. Before scanning, date samples were dried using convective drying at 60 °C and infrared drying at 60 °C with a frequency of 50 Hz, and then they were scanned. The scanning trials were performed for two hundred date palm fruit in fresh, convective-dried, and infrared-dried forms of each cultivar using a flatbed scanner. The image-texture parameters of date fruit were extracted from images converted to individual color channels in RGB, Lab, XYZ, and UVS color models. The models to classify fresh and dried samples were developed based on selected image textures using machine learning algorithms belonging to the groups of Bayes, Trees, Lazy, Functions, and Meta. For both the ‘Mejhoul’ and ‘Boufeggous’ cultivars, models built using Random Forest from the group of Trees turned out to be accurate and successful. The average classification accuracy for fresh, convective-dried, and infrared-dried ‘Mejhoul’ reached 99.33%, whereas fresh, convective-dried, and infrared-dried samples of ‘Boufeggous’ were distinguished with an average accuracy of 94.33%. In the case of both cultivars and each model, the higher correctness of discrimination was between fresh and infrared-dried samples, whereas the highest number of misclassified cases occurred between fresh and convective-dried fruit. Thus, the developed procedure may be considered an innovative approach to the non-destructive assessment of drying impact on the external quality characteristics of date palm fruit.