Background and Objectives: The novel double-pigtail catheter (DPC) has an additional pigtail coiling at the mid-shaft with centripetal multiple side holes. The aim of the present study was to investigate the advantages and efficacy of DPC in overcoming the complications of conventional single-pigtail catheters (SPC) used to drain pleural effusion. Materials and Methods: Between July 2018 and December 2019, 382 pleural effusion drainage procedures were reviewed retrospectively (DPC, n = 156; SPC without multiple side holes, n = 110; SPC with multiple side holes [SPC+M], n = 116). All patients showed shifting pleural effusion in the decubitus view of chest radiography. All catheters were 10.2 Fr in diameter. One interventional radiologist performed all procedures and used the same anchoring technique. Complications (dysfunctional retraction, complete dislodgement, blockage, and atraumatic pneumothorax) were compared among the catheters using chi-square and Fisher’s exact tests. Clinical success was defined as improvement in pleural effusion within 3 days without additional procedures. A survival analysis was performed for calculating the indwelling time. Results: The dysfunctional retraction rate of DPC was significantly lower than that of the other catheters (p < .001). Complete dislodgement did not occur in any of the DPC cases. The clinical success rate of DPC (90.1%) was the highest. The estimated indwelling times were nine (95% confidence interval [CI]: 7.3–10.7), eight (95% CI: 6.6–9.4), and seven (95% CI: 6.3–7.7) days for SPC, SPC+M, and DPC, respectively, with DPC showing a significant difference (p < .05). Conclusions: DPC had a lower dysfunctional retraction rate compared to conventional drainage catheters. Furthermore, DPC were efficient for pleural effusion drainage with a shorter indwelling time.