For 2 years i have deep aching headache /toothache like travelling pains below my cheekbones , these are worse at night. can hardly sleep. history of dental malpractice: resulting in caldwell luc surgery to drain dental debris; poor root fillings resulti

Get evaluated: This may or may not be related to the malpractice. I would start with an ENT doctor to get fully evaluated. I would then see an oral surgeon and an endodontist to cover all the basis. Would be very interested in the finding so keep in touch via health tap.

Question?: Not sure what the question here is. Truthfully, this doesn't necessarily sound like something related to any kind of past dental treatment, but could rather be some sort of TMJ problem that is completely unrelated. Without a complete exam it would be difficult to say, but i would caution you not to be too quick to jump to the assumption that past and current problems are necessarily related.

Different causes: What your describing could be from a variety or combination of different issues. 1. Stress, clenching grinding can strain the muscles that attach to the cheek bone and cause persistaant aches. 2. Sinus issues or allergies. (typically doesn't last 2 years). 3. Tooth issue. See your dentist for eval to r/o dental problem or grinding. Try a a night guard? You may want to see ENT for a sinus scan too.