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We report the case of a 28-year-old transgender (male-to-female) patient that had a partial tear of the rhomboid major tendon, scapulothoracic bursitis, and glenohumeral instability on the same side. These conditions resulted from traumatic events during circus acrobatic maneuvers. Additional aspects of this case that make it unique include (1) the main traumatic event occurred during a flagpole exercise, where the patient’s trunk was suspended horizontally while a vertical pole was grasped with both hands, (2) headaches were associated with the periscapular injury and they improved after scapulothoracic bursectomy and rhomboid tendon repair, (3) surgical correction was done during the same operation with an open anterior capsular-labral reconstruction, open scapulothoracic bursectomy without bone resection, and rhomboid tendon repair, (4) a postoperative complication of tearing of the serratus anterior and rhomboid muscle attachments with recurrent scapulothoracic pain occurred from patient noncompliance, and (5) the postoperative complication was surgically corrected and ultimately resulted in an excellent outcome at the one-year final follow-up.