We describe a case of a bilateral stress fracture of the carpal scaphoid in a 13-year-old boy. The patient played as a goalkeeper from the age of 5 years and presented with a 2-year history of intermittent pain in both wrists. Our patient underwent open reduction and bone grafting from the iliac crest in both wrists (6 months apart). He subsequently became asymptomatic and resumed sport activities. This patient presented with what was considered a rare case of a stress fracture of both scaphoid bones secondary to repetitive dorsiflexed movements. The patient denied the presence of acute symptoms after a fall and did not perceive the onset of pain as being related to any trauma to the wrist, particularly while playing soccer. A review of other similar cases previously published is also presented.