Eyelid tumors accounts for 5–10% of skin tumors. It is important but difficult to identify malignant eyelid tumors from benign lesions in a cost-effective way. Traditional screening methods for malignancy in eyelid tumors require laborious and time-consuming histopathological process. Therefore, we aimed to develop a deep learning (DL)-based image analysis system for automatic identification of benign and malignant eyelid tumors. Using a common digital camera, we collected clinical images from patients who were histopathologically diagnosed with eyelid tumors. We trained 8 convolutional neural network (CNN) models to identify benign and malignant eyelid tumors, including ResNet-50, ResNet-101, InceptionV3, and InceptionResNetV2. Another group of patients with eyelid tumors were also collected as the prospective validation dataset. Performance of DL models and human clinicians in prospective validation dataset were evaluated and compared. A total of 309 images from 209 patients were used for training DL system, all eight models reached an average accuracy greater than 0.958 in the internal cross-validation. 36 images from 36 patients were included for the prospective validation, the models reached the best performance in accuracy, sensitivity, specificity, and area under curve (AUC) of 0.889 (95% CI 0.747–0.956), 0.933 (95% CI 0.702–0.988), 0.857 (95% CI 0.654–0.950), and 0.966 (95% CI 0.850–0.993), respectively. DL system had a similar performance as the senior ophthalmologists, and outreached the performance of junior ophthalmologists and medical students. DL system can identify benign and malignant tumors through common clinical images, with a better performance than most ophthalmologists. Combining DL system with smartphone may enable patients’ self-monitoring for eyelid tumors and assist in doctors’ clinical decision making.