The emergence of new technologies focusing on “computer vision” has contributed significantly to the assessment of fruit quality. In this study, an innovative approach based on image analysis was used to assess the external quality of fresh and frozen “Mejhoul” and “Boufeggous” date palm cultivars stored for 6 months at −10 °C and −18 °C. Their quality was evaluated, in a non-destructive manner, based on texture features extracted from images acquired using a digital camera and flatbed scanner. The whole process of image processing was carried out using MATLAB R2024a and Q-MAZDA 23.10 software. Then, extracted features were used as inputs for pre-established algorithms–groups within WEKA 3.9 software to classify frozen date fruit samples after 0, 2, 4, and 6 months of storage. Among 599 features, only 5 to 36 attributes were selected as powerful predictors to build desired classification models based on the “Functions-Logistic” classifier. The general architecture exhibited clear differences in classification accuracy depending mainly on the frozen storage period and imaging device. Accordingly, confusion matrices showed high classification accuracy (CA), which could reach 0.84 at M0 for both cultivars at the two frozen storage temperatures. This CA indicated a remarkable decrease at M2 and M4 before re-increasing by M6, confirming slight changes in external quality before the end of storage. Moreover, the developed models on the basis of flatbed scanner use allowed us to obtain a high correctness rate that could attain 97.7% correctness in comparison to the digital camera, which did not exceed 85.5%. In conclusion, physicochemical attributes can be added to developed models to establish correlation with image features and predict the behavior of date fruit under storage.