Background: Post-dural puncture headache is a known complication of neuraxial anesthesia and acute subdural hematoma has been associated with unintentional dural puncture. Notably, a significant number of unintentional dural punctures remain unidentified. We present two contrasting cases of subdural hematoma (SDH) following labour epidural anesthesia with no sign of dural puncture at time of anesthesia. Patient 1 presented with headache post-partum day (PPD) six, SDH was identified PPD23, and blood-patch treatment performed PPD35. Patient 2 presented with headache immediately, had SDH identified PPD3, and placement of blood-patch PPD4. Methods: The cases are presented and the literature was reviewed for prior cases. Results: Patient 1 developed significant bilateral SDH with severe headache and right abducens palsy. Headache resolved post blood patch however surgical evacuation was required and the abducens palsy persisted. Patient 2 experienced resolution of symptoms two days post blood patch, the small unilateral SDH was managed conservatively, and had no neurological deficits. Conclusions: Headache is common in the postpartum period. The majority are primary etiology and benign. SDH is a rare but serious complication of neuraxial anesthesia, and the consequences may be devastating. Rapid identification and early treatment are essential to avoid severe neurological sequelae.