To present the clinical and radiographic data, emphasize our surgical technique and how it was used, and the outcome measures in a case series of patients with chronic symptomatic peroneal sheath pain. A retrospective chart and radiograph review was conducted involving 36 adolescent patients (ages 8 to 20 y) treated surgically for chronic symptomatic peroneal sheath pain from 2010 to 2020. Findings that include chief complaint, magnetic resonance imaging findings, and surgical measures were documented. The patients’ postoperative and clinic visit notes were analyzed and outcome scores (FAOS Foot & Ankle Survey, AOFAS Ankle-Hindfoot Scale, and Kaikkonen Functional Scale) were calculated to determine the long-term results of the procedure. In our case series of 36 patients undergoing surgical treatment for chronic symptomatic peroneal sheath pain the procedures performed were as follows: 35 peroneal sheath repairs (97.22%), 34 ankle arthroscopies (94.44%), 27 resections of anomalous peroneus brevis muscle belly (75.00%), 2 resections of accessory peroneus quartus muscle (5.56%), 7 partial synovectomies (19.44%), 29 debridements (80.56%), and 6 Brostrom repairs (16.67%). magnetic resonance imaging findings showed 50% of our patient population had low-lying peroneus brevis muscles, and on examination during surgery, 61.11% of peroneus brevis muscles extended past the fibular tip. The average time in the cast post-operatively was 4.33 weeks. The average time from surgery to return to activity was 9.03 weeks. Twenty-two of the 36 patients (61.11%) were athletes and 100% were able to return to their sport. Outcome scores were retrospectively determined to be 99.27 for the FAOS Foot and Ankle Survey, 98.72 for the AOFAS Ankle-Hindfoot Scale, and 99.31 for the Kaikkonen Functional Scale. Complications were minimal and included 1 postoperative infection, 3 cast impingements, and 2 reported instances of post-operative pain. In our retrospective case series of 36 patients, the outcomes of surgical intervention for peroneal tendon pathology unresponsive to nonsurgical management in pediatric patients were evaluated. Our surgical method utilizes debridement, synovectomy, excision of low lying peroneus brevis muscle belly, excision of peroneus quartus if present, repair of split-tears of the tendons, and repair of the peroneal tendon sheath using “pants over vest” sutures to tighten the sheath. Our chart review shows all 36 patients were satisfied with the outcome, demonstrated improvement in relevant patient-reported outcome measures, and would elect to undergo the procedure again. Therefore, the novel surgical techniques outlined in this study appear to be viable options to treat chronic symptomatic peroneal tendon sheath pain resistant to conservative methods. Level of Evidence: Retrospective Case Series, Level IV.