Rotator cuff injury comprises a continual spectrum of lesions ranging from tendinopathy, which may progress to partial- or full-thickness tear. This progression may be influenced by the interplay of extrinsic and intrinsic factors. We describe the case of a 29-year-man who presented with right shoulder pain for one year. His initial magnetic resonance (MR) arthrogram showed supraspinatus tendinopathy. Subsequent MR arthrogram, obtained after a road traffic accident, showed a bursal-sided partial-thickness tear of the supraspinatus tendon. In view of his worsening clinical symptoms, surgery was performed ten months later, revealing a full-thickness rotator cuff tear near the tendon insertion, with a tight subacromial space and bony protuberance of the humeral head. The pathogenesis of rotator cuff injuries, the roles of different imaging modalities in the diagnosis of rotator cuff injuries, as well as the advantages and limitations of various radiological modalities, are discussed.