Two case reports describe simultaneous bilateral Achilles tendon rupture in healthy athletes. This injury has not been previously reported as an acute injury in healthy patients. Isolated bilateral ruptures have occurred in patients receiving long-term corticosteroid therapy. Achilles tendons that have been exposed to chronic wear from repeated stress generated through physical activity show evidence of degeneration in their microstructure and are more prone to rupture than are healthy tendons. Specific bilateral forces generated through the Achilles tendons of experienced older gymnasts predispose these persons not only to chronic bilateral tendon wear but also to acute bilateral simultaneous ruptures during specific maneuvers.