Post-dural puncture headache (PDPH) is a common complication of epidural and spinal anaesthesia in obstetric medicine. In rare cases, PDPH can be associated with complications such as cerebral venous thrombosis (CVT) as well. We discuss a recent case of a young female who developed PDPH and CVT concurrently after undergoing epidural anaesthesia for initially uncomplicated labour and delivered via an emergency caesarean section. She developed an orthostatic headache a few hours post administration of the epidural anaesthetic, which was initially treated as a suspected PDPH by giving simple analgesia and caffeine. Her symptoms did not improve and she underwent further neuroimaging, which revealed the development of a CVT. Despite the prompt administration of enoxaparin, the headache persisted and did not respond to increased doses of analgesia. After deliberation and inter-departmental discussion, an epidural blood patch was performed, leading to the prompt resolution of the headache. This report highlights a rare concurrence of PDPH and CVT, causing a diagnostic dilemma that resulted in treatment delays for the patient. Treating both conditions raises difficult practical questions, especially regarding the use of an epidural blood patch as opposed to anticoagulation. Given the risk of fatal complications such as venous cerebral infarction, seizures, and subdural hematoma, prompt treatment of both PDPH and CVT is strongly recommended. The multifactorial mechanism by which CVT develops with intracranial hypotension and PDPH also makes it essential for clinicians to keep an open mind when managing post-caesarean headaches, requiring inter-departmental cooperation to ensure optimal patient outcomes.