"To know the times" means to know the enemy's disposition in battle. Is is flourishing or waning? By observing the spirit of the enemy's men and getting the best position, you can work out the enemy's disposition and move your men accordingly.

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Quote text and notes from Wikiquote: Miyamoto Musashi (page history), available under CC BY-SA 4.0. Source quality and labels are our own summary of what Wikiquote records.