Spinal cord stimulation (SCS) is a minimally invasive therapy that is increasingly used to treat refractory neuropathic pain. Although this technique has a low incidence of serious long-term adverse sequelae, the risk of complications such as inadvertent dural puncture remains. The goal of this article was to determine the impact of the contralateral oblique (CLO) fluoroscopic view incidence of postdural puncture headache (PDPH) during spinal cord stimulator implantation as compared to lateral fluoroscopic view. This was a single academic institution retrospective analysis of electronic medical records spanning an approximate 20-year time period. Operative and postoperative notes were reviewed for details on dural puncture, including technique and spinal level of access, the development of a PDPH, and subsequent management. Over nearly two decades, a total of 1637 leads inserted resulted in 5 PDPH that were refractory to conservative measures but responded to epidural blood patch without long-term complications. The incidence of PDPH per lead insertion utilizing loss of resistance and lateral fluoroscopic guidance was 0.8% (4/489). However, adoption of CLO guidance was associated with a lower rate of PDPH at 0.08% (1/1148), p < 0.02. The incorporation of the CLO view to guide epidural needle placement can decrease the odds of a PDPH during percutaneous SCS procedures. This study further provides real-world data supporting the potential enhanced accuracy of epidural needle placement in order to avoid unintentional puncture or trauma to deeper spinal anatomic structures.