Periodic breast cancer screening with mammography is considered effective in decreasing breast cancer mortality. For screening programs to be successful, an intelligent image analytic system may support radiologists’ efficient image interpretation. In our previous studies, we have investigated image retrieval schemes for diagnostic references of breast lesions on mammograms and ultrasound images. Using a machine learning method, reliable similarity measures that agree with radiologists’ similarity were determined and relevant images could be retrieved. However, our previous method includes a feature extraction step, in which hand crafted features were determined based on manual outlines of the masses. Obtaining the manual outlines of masses is not practical in clinical practice and such data would be operator-dependent. In this study, we investigated a similarity estimation scheme using a convolutional neural network (CNN) to skip such procedure and to determine data-driven similarity scores. By using CNN as feature extractor, in which extracted features were employed in determination of similarity measures with a conventional 3-layered neural network, the determined similarity measures were correlated well with the subjective ratings and the precision of retrieving diagnostically relevant images was comparable with that of the conventional method using handcrafted features. By using CNN for determination of similarity measure directly, the result was also comparable. By optimizing the network parameters, results may be further improved. The proposed method has a potential usefulness in determination of similarity measure without precise lesion outlines for retrieval of similar mass images on mammograms.