Trigeminal Neuralgia: This condition is characterized by recurrent episodes of severe, shooting pain in the face, particularly in the areas supplied by the trigeminal nerve, which includes the jaw and cheek. The pain is often triggered by actions such as chewing, brushing teeth, or even light touch, matching the patient's symptoms.

Temporomandibular Joint (TMJ) Disorder: While TMJ disorders typically cause more of a dull ache, some patients can experience sharp pains, especially if there is an acute component such as a disc displacement or if the patient has a history of bruxism.
Dental Issues: Problems like abscesses, cracked teeth, or severe decay can cause sharp, severe pain, especially when chewing or brushing teeth. However, these conditions usually have other accompanying symptoms like sensitivity to temperature or swelling.
Glossopharyngeal Neuralgia: This is a rare condition but can cause sharp, stabbing pain in the tongue, throat, ear, and area of the jaw, triggered by actions like swallowing or chewing.

Multiple Sclerosis: Although less common, facial pain can be an initial presenting symptom of multiple sclerosis, particularly if it's associated with other neurological symptoms. It's crucial to consider this diagnosis to avoid missing a potentially treatable condition.
Stroke or Transient Ischemic Attack (TIA): While facial pain is not a typical symptom of stroke or TIA, it can occur, especially if the pain is accompanied by other neurological deficits. Given the patient's history of hypertension, this is a critical diagnosis not to miss.
Cancer: Tumors affecting the face or trigeminal nerve can cause severe facial pain. Although rare, missing a diagnosis of cancer could have significant consequences.

Short-Lasting Unilateral Neuralgiform Headache Attacks with Conjunctival Injection and Tearing (SUNCT) / Short-Lasting Unilateral Neuralgiform Headache Attacks with Autonomic Features (SUNA): These are rare headache disorders that can cause severe, stabbing pain, usually around the eye, but can sometimes involve the face.
Eagle Syndrome: This condition involves an elongated styloid process or calcified stylohyoid ligament, which can cause sharp, stabbing pain in the face and throat, often triggered by swallowing.
Raeder Syndrome: A rare condition characterized by a combination of facial pain, miosis, and ptosis, usually due to a lesion affecting the sympathetic nerves in the face.