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Background: Insertional Achilles tendinopathy (IAT) is a common cause of chronic posterior heel pain. Surgical intervention reproducibly improves patients’ pain and functional status. We hypothesized that patients older than 60 years would have similar improvements in pain and function and low rates of complications after surgery for IAT when compared to a younger cohort. Methods: Retrospective review of adult case series in patients undergoing surgical management of IAT. Patients were stratified into those 60 years and younger and those older than 60 years. Patients with prior or concomitant surgical procedures and revisions were excluded. Visual analog scale (VAS), Short Form–36 Physical Component Summary and Mental Component Summary (SF-36 PCS/MCS) scores, wound infection, and recurrence, defined as a redevelopment of heel pain in the operative extremity within 6 months, were assessed with a minimum follow-up of 12 months. Statistical analysis was performed using linear regression mixed models and χ 2 analysis. Thirty-seven patients were enrolled, with 38 operative heels. The younger cohort had an average age of 49.1 (range, 26-60) years. The older group had an average age of 66.8 (range, 61-76) years. Results: VAS and SF-36 PCS scores for the entire cohort significantly improved at 6 and 12 months postoperatively ( P < .001). Postoperative SF-36 MCS scores for the cohort significantly improved only at 12 months ( P < .001). No significant differences between the young and elderly were seen with regard to improvements in VAS and SF-36 PCS/MCS at 6 or 12 months postoperatively. Multiple linear regression models showed no significant difference between age groups and VAS score, SF-36 PCS/MCS, or change in pain scores after controlling for comorbidities. No significant difference in overall complication rates was seen between the 2 groups (4.9% vs 29.4%, P = .104). There was 1 recurrence of heel pain in the younger group and 4 recurrences of pain in the older group (23.5%) at 6 months, of which 2 resolved at 1 year. There was 1 case of a superficial wound infection requiring antibiotics in the older cohort (5.9%). No patients required surgical revision. Conclusion: Surgical management of IAT in an older population produced similar improvements in clinical results when compared to a younger cohort, with no significant increase in postoperative complications. Level of Evidence: Level III, retrospective comparative series.