Study Design. Observational study. Objective. To identify associations between preoperative symptom duration and postoperative patient satisfaction. Summary of Background Data. Sciatica due to lumbar disk herniation (LDH) is a cause of disability and reduced quality life. Patients with severe pain and disability or were recovery is unacceptably slow, surgical intervention can be advised. For these patients, evidence-based recommendations on the timing of the surgical intervention needs to be established. Methods. All patients who underwent discectomy at a Spine Centre, due to radicular pain from June 2010 to May 2019 were included. Pre- and postoperative data including demographic data, smoking, consumption of pain medication, comorbidity, back and leg-pain, health-related quality of life as measured by EQ-5D, ODI, previous spine surgery, sick leave, and duration of back and leg-pain before surgery were utilized. The patients were divided into four groups based on their self-reported duration of leg-pain before surgery. To minimize baseline differences between the groups, propensity-score matching was employed in a 1:1 fashion, balancing the groups on all reported preoperative factors. Results. Of 1607 patients undergoing lumbar discectomy, four matched cohorts based on their self-reported duration of leg-pain before surgery were created. Each cohort consisted of 150 patients well balanced on preoperative factors. Overall 62.7% of the patients were satisfied with the surgical result ranging from 74.0% in the <3 months group to 48.7% in the >24 months group (P<0.000). The portion of patients achieving a minimum clinically important difference for EQ-5D decreased from 77.4% with early intervention to 55.6% in the late group (P<0.000). The number of surgical complications were not affected by the duration of preoperative leg-pain. Conclusion. We found significant difference in patient satisfaction and health-related quality of life in patients related to the duration of preoperative leg-pain due to symptomatic LDH. Level of Evidence. 3.