With a high complication and mortality rate, intra-sphenoidal and transorbital trauma poses a high complication rate and remains challenging to manage. Numerous key structures run nearby such as: the optic nerve, internal carotid arteries and ophthalmic arteries. The authors present the case of a 75-year-old gentleman, with hypertension and no past ocular history, who presented to the emergency department after tripping and hitting his head on a branch on the sidewalk. Examination revealed a 2cm long laceration of the lateral superior cheek with a wooden foreign object. Moreover, examination was difficult because of periorbital swelling, hyperglobus, ophthalmoplegia and mechanical blepharoptosis. Furthermore, there was a left relative afferent pupillary defect (RAPD), exotropia, exophthalmos and no light perception. Slit-lamp examination showed: conjunctival injection, a clear cornea and a normal anterior chamber. Dilated fundoscopy revealed no significant findings. The authors attached an image of the foreign body, patient’s left eye, frontal and sagittal computed tomography scan of orbits and sinus, and an optical coherence tomography scan. The foreign body was found to have penetrated the left orbit inferiolaterally and inferior to the inferior rectus muscle. It penetrated the orbital wall into the sphenoid sinus without penetrating the posterior wall and was found to be 6mm away from the internal carotid artery. Additionally, fractures in the orbital floor, medial and inferior to the foreign object, were noted. Removal of the foreign object was performed under CT-guided endoscopic surgery and the patient was discharged three days after with co-amoxiclav. On follow-up six months later, his visual acuity had improved to 0.4, however there was still a left RAPD as well as affected colour vision. After examination, a diagnosis of traumatic optic neuropathy was made. Recommendations for handling similar trauma cases are centred on access to a specialised trauma team with imaging and experienced surgeons. Given the sparse number of cases of penetrating orbital trauma, this case report has highlighted the complications and challenges involved in transorbital and intra-sphenoidal penetrating trauma.