We describe an elite youth football player who developed lateral foot pain of previously unknown origin. A thorough patient history and physical examination, as well as an in-depth presentation of radiographic findings on computed tomography and magnetic resonance imaging scans were performed. Through this combination, the puzzle was resolved and a rare peroneus longus tendinopathy due to bony spurs in the cuboid groove was diagnosed. A peroneus longus exploration and release and reduction of the cuboidal bone spurs were performed, and an intensive rehabilitation phase followed. The patient successfully returned to performance and set a career in professional football.