A middle-aged man developed sequential episodes of transient osteoporosis of the hip (TOH) following semaglutide exposure, with symptoms resolving after drug discontinuation. TOH presents as acute hip pain with bone marrow edema but typically self-resolves. The temporal relationship between drug exposure and symptom onset occurred twice, suggesting a potential mechanistic connection rather than coincidence. This represents the first reported musculoskeletal complication potentially linked to semaglutide, a GLP-1 receptor agonist increasingly prescribed off-label for weight loss. The finding warrants attention given semaglutide's explosive growth in clinical use, with millions now taking the drug primarily for obesity management. While TOH is rare and self-limiting, acute hip pain can significantly impact mobility and quality of life. The mechanism remains unclear, though GLP-1 receptors exist in bone tissue and may influence bone metabolism. This single case report cannot establish causation, and the temporal association could be coincidental. However, the pattern of symptom onset, resolution, and recurrence with re-exposure creates a compelling clinical narrative that merits systematic investigation across larger patient populations taking semaglutide.