Pseudoangiomatous stromal hyperplasia (PASH) is a benign breast disorder with the tumoral variety being extremely rare. We report a rare case of synchronous, massive axillary and breast tumoral PASH in a 55-year-old post-menopausal woman. Mammography, ultrasonography and sonoelastography features are illustrated with histopathological correlation. A high-grade invasive ductal carcinoma was detected in the contralateral breast on annual follow-up imaging. Radiologists need to be familiar with the imaging appearances of PASH and be aware of its association with subsequent cancer risk. To the best of our knowledge, the present case of synchronous tumoral PASH in the breast and axillary tissue is the second reported case till now.