Although there have been reports of the successful diagnosis of skin disorders using deep learning, unrealistically large clinical image datasets are required for artificial intelligence (AI) training. We created datasets of standardized nail images using a region-based convolutional neural network (R-CNN) trained to distinguish the nail from the background. We used R-CNN to generate training datasets of 49,567 images, which we then used to fine-tune the ResNet-152 and VGG-19 models. The validation datasets comprised 100 and 194 images from Inje University (B1 and B2 datasets, respectively), 125 images from Hallym University (C dataset), and 939 images from Seoul National University (D dataset). The AI (ensemble model; ResNet-152 + VGG-19 + feedforward neural networks) results showed test sensitivity/specificity/ area under the curve values of (96.0 / 94.7 / 0.98), (82.7 / 96.7 / 0.95), (92.3 / 79.3 / 0.93), (87.7 / 69.3 / 0.82) for the B1, B2, C, and D datasets. With a combination of the B1 and C datasets, the AI Youden index was significantly (p = 0.01) higher than that of 42 dermatologists doing the same assessment manually. For B1+C and B2+ D dataset combinations, almost none of the dermatologists performed as well as the AI. By training with a dataset comprising 49,567 images, we achieved a diagnostic accuracy for onychomycosis using deep learning that was superior to that of most of the dermatologists who participated in this study.