Spinal anaesthesia, though safe, poses a risk of post-dural puncture headache (PDPH), with its incidence and risk factors undocumented in Botswana. A prospective cross-sectional study of 600 cesarean section patients (February–July 2024) was conducted. PDPH was diagnosed using the International Headache Society guidelines. Independent variables included age, BMI, care provider experience, number of spinal anaesthesia attempts, and previous history of PDPH, with PDPH as the dependent variable. A total of 600 patients successfully underwent spinal anaesthesia for cesarean sections. The median age, weight, and height were 30 years, 73.0 kg, and 1.6 meters, respectively, with 80.0% having a BMI > 24.9. The overall PDPH rate was 11.8%. Most PDPH cases occurred within the first 24 hours (66.2%), presenting primarily as mild frontal–occipital headaches (97.2%). A significantly higher rate of PDPH was observed in patients with a history of PDPH (38.9% vs. 14.0%, p = 0.012). Multiparous women experienced a higher rate of PDPH compared to primiparous women (12.7% vs. 9.7%, p = 0.302), though this difference was not statistically significant. Two attempts at spinal anaesthesia were associated with a significantly higher rate of PDPH compared to one attempt (16.7% vs. 8.8%, p = 0.012) and three attempts (16.7% vs. 8.6%, p = 0.023), while no significant difference was observed between one and three attempts (8.8% vs. 8.6%, p = 0.950). PDPH rates did not differ significantly among nurse anaesthetists, medical officers, and residents (p-values 0.547, 0.364, and 0.851, respectively). Additionally, provider experience (<2 years vs. >2 years) did not significantly influence PDPH rates (p = 0.397). The prevalence of PDPH was 11.8%, with a history of PDPH identified as a significant risk factor. Including potential PDPH in the consent process, particularly for patients with a prior history, and implementing procedural refinements may help reduce its occurrence.