Achilles tendon ossification is not a frequent association of posterior heel pain in pain physicians’ daily practice. The condition has been reportedly common following rear heel trauma (repetitive heel stress injury), surgery (club foot surgery); however, some endocrino-metabolic, haematological disorders can also contribute to Achilles tendon ossification. Shape of ossified tendon mass varies from discrete (single/multiple) to extensive variety; and as per literature review, in bilateral cases they are alike. To be intriguing, here in this write-up, we demonstrate asymmetrical (in terms of clinical features and radio-imaging findings), bilateral Achilles tendon ossification in a 70-year-old retired farmer, first time in literature.