I've read accounts where a modern jet pilot went to a doctor and the doctor said he had tons of scarring on his eardrums. Asked if he knew he had blown out his eardrums a lot in his life. He said he didn't know this. Doctor asked him if he ever had a bit of blood in his earphone cups when he took them off after a flight. He said yes, quite often. Doctor said there you go.
So, moral of the story is it could happen quite often, but in the heat of adrenaline-fueled pre-occupation you might not even notice it when it happens.