I would suggest checking to make sure no hair is sticking into his eye area causing irritation.
But its possible he has a corneal injury or clogged tear ducts causing the overflow.
Because he is squinting and acting as if the eyes are painful I would suggest having a vet examine him.
The vet can stain the eye and look for corneal injuries and look into the eye to see if there is any infection or disease. They can also check for tear production volume too. And of course prescribe medication or make treatment suggestions once the exam is done.
Hope this helps you!
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