Context: Supraspinatus tendinopathy and shoulder pain are common in competitive youth swimmers; however, no studies have investigated clinical and structural factors contributing to shoulder pain and disability in master level swimmers. Objective: The objectives of this study were: 1) to determine the prevalence of shoulder pain and disability in master level swimmers, 2) to identify the most provocative special tests for shoulder pain, and 3) to determine if shoulder clinical and tissue specific measures, training variables and volume vary between those with and without shoulder pain, dissatisfaction and disability. Design: Cross-sectional. Setting: Collegiate swimming facilities. Patients or Other Participants: Thirty-nine adult masters level swimmers were evaluated and included in the data analysis. Main Outcome Measures: A survey of demographics, training, and pain and disability ratings using the Penn Shoulder Score and Disability of Arm Shoulder Hand sports module. Swimmers underwent a clinical exam including shoulder passive range of motion (PROM), posterior shoulder endurance test (PSET), supraspinatus tendon structure and posterior capsule thickness. One-way ANOVAs were used to compare demographics, clinical and structural findings between those with significant pain, dissatisfaction and disability (+PDD) and those without (−PDD). Results: Fifteen percent of subjects reported pain at rest, 28% with normal activities (eating, dressing), and 69% with strenuous activities (sports) and 50% reported disability. The +PDD group had less shoulder internal rotation (10°), less ER (8°), and completed less yardage per day and per year. There were significant differences in the supraspinatus tendon structure between the +PDD and –PDD groups. Conclusion: Masters swimmers with pain and disability are able to self-limit yardage and likely why they recorded less yardage. The reduced shoulder motion (IR and ER) without posterior capsule differences may be due to rotator cuff muscle/tendon restrictions and the supraspinatus tendon structure may indicate degeneration caused by previous overuse resulting in pain.