Aim: Malignant ureteral obstruction (MUO) is a serious complication of advanced-stage malignancies, associated with limited life expectancy and lacking standardized management guidelines. This study aims to compare the technical and clinical success rates, as well as the complication profiles, of retrograde ureteral stenting (RUS) and antegrade ureteral stenting (AUS)—including its single-and multi-stage subtypes—in the treatment of MUO. Materials and Methods: In this retrospective single-center study, 127 patients (155 procedures) who underwent ureteral stenting for MUO between 2019 and 2023 were analyzed. Patients were divided into RUS and AUS groups. AUS procedures were further categorized into single-stage (tubeless) and multi-stage (with protective nephrostomy) subgroups. Technical success, clinical success, complication rates, and etiological data were evaluated and statistically compared. Results: Technical success was significantly higher in the AUS group (97.6%) compared to the RUS group (37.7%) (p < 0.001). No significant difference was found in clinical success between the groups. AUS maintained high technical success regardless of intrinsic or extrinsic etiology. Although single-stage AUS demonstrated a slightly higher clinical success rate, complication and success rates between single-and multi-stage AUS procedures did not differ significantly. No major complications were observed across the AUS subgroups. Conclusions: AUS is a highly effective and safe intervention for MUO, outperforming RUS in terms of technical success. When appropriately selected, single-stage AUS offers a less invasive and cost-effective alternative without compromising outcomes. These findings support the broader implementation of single-stage AUS as a first-line option in the management of MUO.