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I was reading Tom Brown's School Days, and I came across the part where they were describing a sport called backswording, in which the competitors will have their left hand tied to their leg/back, and they will be armed with a stick with their right arm. The aim of the game, is to break the head of your opponent, who is also tied up and armed in like manner.

I am not sure how much damage is being done, when someone "breaks" his opponent's head. Does he really crack his skull and break his head? or does he just "break" the skin of his head?

In both cases, blood must flow, that I know, and the loser of the game is when any amount of blood, no matter how little, flows down his forehead, or anywhere above his eyebrows, and is seen.

So, going back to my question, what exactly does "break one's head" mean?

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When I was young (London, in the 60's) "crack one's head open" was a common expression, which I found disturbing and I imagined horrible wounds.

When I cut my head on the corner of a desk at school, and needed stitches, I was distressed to hear the teacher tell my mother on the phone "he's cracked his head open", because I was concerned that she would think it was much worse than it was.

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You've answered your own question:

The loser of the game is when any amount of blood, no matter how little, flows down his forehead, or anywhere above his eyebrows, and is seen.

It is certainly clear from that context that break one's head means to bleed from the head. I am not sure that this is (or was) an established idiom. NGrams certainly shows some usage for variants on the phrase:

NGrams for break my head

I suspect that most uses are referring to breaking the skin but I didn't check.

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    I know that my head will bleed, I'm asking, will it bleed because the skull has cracked, or did the skin just scratch, and thus bleed?
    – Thursagen
    Commented Aug 19, 2011 at 13:00
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    @Thursagen The scalp is notorious for bleeding wounds. It is because the skin ruptures, and not because of the skull cracking. The human skull is pretty hard, and it takes a lot of force to break it. The human scalp, by contrast, is very thin, and contains a lot of blood.
    – Beofett
    Commented Aug 19, 2011 at 13:05
  • @Thursagen: It doesn't matter. The point is the bleeding. If it bleeds, it qualifies.
    – MrHen
    Commented Aug 20, 2011 at 0:09

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