If the 'cups' have blown out of the engine block (they're actually called core plugs) then I would imagine the cooling system is pressurising. Possible cause cyl head gasket, or cracked cyl head. You say you can see oil at the head, so this confirms head gasket gone. This pressure in the cooling system maybe what has caused the cracked transmission oil cooler. Petrol and matches !! Regards Don
Don., March 2010