RolfAndreassen comments on Rationality Quotes December 2012 - Less Wrong
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In context, this particular quote seems to be talking more about large-scale battles than individual duels. So, if you've already launched your cavalry at the enemy twice, and they were driven off in disarray each time, then another try is probably not going to work even if your enemy doesn't expect it.
I didn't see any discussion of strategy or leadership in the Book of the Five Rings.
I have, however, seen many cases in competitive gaming where correctly judging what my opponent was expecting me to do allowed me to counter them more effectively. There are a large number of meta-levels there, and operating two levels above your opponent is typically as bad as operating one level below them.
It appears to me that Musashi intends his principles to be applicable to either duel or battle. There are several illustrations that imply that he is not just talking about duels:
I suspect that 'flanks' might be a more idiomatic translation of that last. But at any rate it is clear that Musashi does not limit his advice to individual combat.