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This is equivalent to 0-500 experience points if you win against everyone. Also, they might not completely reduce your health to zero, as Eisen's regeneration won't fully restore your health, and the opponent might have weak attacks that don't remove a full health point. So, there is a risk, although it's relatively small.
Ryohei orders a Dunkler Wolf and drowns his sorrow over the defeat, while also observing what's happening in the bar.