Purpose To compare outcome following continuation of conservative interventions with surgery in patients with chronic recalcitrant Medial Tibial Stress Syndrome (MTSS). Methods Patients with chronic leg pain underwent physical examination and an intracompartmental muscle pressure (ICP) in a tertiary referral center. MTSS was diagnosed by a suggestive history and physical examination and normal ICP of the deep posterior compartment. Patients were offered continuation of conservative treatment or surgery. Patient characteristics, symptom scores (Verbal Rating Scale, range 1‐5) and sports participation before and at least one year later were collected using questionnaires. Success was defined as a good or excellent outcome. Results A total of 883 patients underwent an ICP between January 2013 and March 2019. Sixty‐five patients were diagnosed with MTSS and fulfilled inclusion criteria (surgery n = 19, conservative n = 46). At intake, gender, age and level of sports participation were comparable, but symptom duration was significantly longer in the surgical group (40 ± 24 versus 25 ± 21 months; P <0.02). At follow‐up, surgical treatment reduced intensity of tightness more effectively, both in rest (surgical −1.0 ± 0.2 vs conservative −0.3 ± 0.2; P =0.04) and during exercise (surgical −1.0 ± 0.3 vs conservative −0.3 ± 0.2; P =0.04). Total symptom scores during exercise dropped more following surgery (surgery −23 ± 19 vs conservative −11 ± 18; P =0.02), and more surgically treated patients returned to physical activity (surgical 74% vs conservative 65%; P =0.04). Success rates were similar (surgical 47% vs conservative 28%; P =0.16). Conclusion Some patients with chronic recalcitrant MTSS may benefit from surgical treatment. Future studies should focus on identifying patient factors legitimizing surgery.