Osteoarthritis (OA) is the most common arthritis and the leading cause of lower extremity disability in older adults. Understanding OA progression is important in the development of patient-specific therapeutic techniques at the early stage of OA rather than at the end stage. Histopathology scoring systems are usually used to evaluate OA progress and the mechanisms involved in the development of OA. This study aims to classify the histopathological images of cartilage specimens automatically, using artificial intelligence algorithms. Hematoxylin and eosin (HE)- and safranin O and fast green (SafO)-stained images of human cartilage specimens were divided into early, mild, moderate, and severe OA. Five pre-trained convolutional networks (DarkNet-19, MobileNet, ResNet-101, NasNet) were utilized to extract the twenty features from the last fully connected layers for both scenarios of SafO and HE. Principal component analysis (PCA) and ant lion optimization (ALO) were utilized to obtain the best-weighted features. The support vector machine classifier was trained and tested based on the selected descriptors to achieve the highest accuracies of 98.04% and 97.03% in HE and SafO, respectively. Using the ALO algorithm, the F1 scores were 0.97, 0.991, 1, and 1 for the HE images and 1, 0.991, 0.97, and 1 for the SafO images for the early, mild, moderate, and severe classes, respectively. This algorithm may be a useful tool for researchers to evaluate the histopathological images of OA without the need for experts in histopathology scoring systems or the need to train new experts. Incorporating automated deep features could help to improve the characterization and understanding of OA progression and development.