Background: Upper lumbar disc herniation (ULDH), affecting the L1–L2 and L2–L3 levels, is relatively uncommon but often presents with atypical symptoms, making diagnosis and treatment challenging. Given its proximity to the conus medullaris and the narrower spinal canal in the upper lumbar region, even small disc herniations can produce significant neurological deficits. Aim: This study aimed to evaluate the clinical characteristics, surgical management, and outcomes of patients with ULDH treated at a tertiary care hospital in Bangladesh. Method: A retrospective review was conducted on 100 patients diagnosed with ULDH and treated surgically at a Tertiary Medical College Hospital in Bangladesh from January 2020 to December 2020. Patient data including demographics, presenting symptoms, radiological findings, surgical technique, and postoperative outcomes were analyzed. All patients underwent microdiscectomy or laminectomy based on clinical and radiological findings. Follow-up was conducted for six months postoperatively. Results: The mean age was 52.4 ± 11.6 years, with a male predominance (61%). Most patients presented with anterior thigh pain (78%), lower limb weakness (42%), and bladder dysfunction (12%). The most common disc level affected was L2–L3 (67%). Microdiscectomy yielded better recovery in patients with isolated disc herniation, while laminectomy was used for calcified or migrated discs. Significant improvement in VAS and ODI scores was noted postoperatively (p < 0.001). Only 5% of patients developed complications such as dural tear or superficial wound infection. Conclusion: ULDH, though rare, presents unique diagnostic and surgical challenges. Early surgical intervention tailored to the disc pathology results in favorable neurological and functional outcomes. Recognizing its atypical symptoms and imaging findings is crucial for timely and effective treatment.