The widely practiced sport of cycling presents unique biomechanical challenges leading to distinct injury patterns. This review explores the biomechanics of cycling, correlates them with common injuries, and discusses the imaging findings associated with these conditions. We focus on overuse injuries, acute traumatic injuries, and specific pathophysiologic mechanisms underlying these conditions. Emphasis is placed on the role of magnetic resonance imaging in diagnosis and management, highlighting how sport-specific biomechanics influence injury patterns and imaging appearances.