Extensor hallucis longus tendon injury is relatively rare and is principally caused by a laceration when a sharp object is dropped on the instep. Primary suturing is possible if the injury is acute, but if the tear is chronic, tendon contracture causes the space between the edges of the tear to widen, disrupting the end-to-end connection. In particular, a claw toe or checkrein foot deformity may develop over time due to adhesion of the lower leg tendons near the fracture site or scar. We report on a 44-year-old man who visited our outpatient clinic complaining of pain in the right foot and a hindered ability to extend his great toe. He had enjoyed playing soccer during his schooldays; since that time, the extension of that toe had become somewhat difficult. T2-weighted sagittal magnetic resonance imaging revealed that the continuity of the extensor hallucis longus tendon had been lost at the distal phalangeal base attachment site, and that the region of the proximal tendon was retracted to level of the middle shaft of the proximal phalanx. The findings allowed us to diagnose extensor hallucis longus tendon rupture accompanying osteoarthritic changes in the joint and soft tissues. We performed surgical tenorrhaphy and adhesiolysis. This is a rare case of extensor hallucis longus tendon rupture caused by minor trauma. Arthritis that developed at a young age caused the adhesions. If patients with foot and ankle arthritis show tendon adhesion at the arthritic site, tendon rupture can develop even after minor trauma or intense stretching.