Yes, in episode 143. He fought Sasuke and his team, while not being serious. He broke Sasuke's Mangekyou sharingan and the lariated Sasuke, that's, after sticking Sasuke with all his sWord previous. Sasuke survived because Karin healed him. Killerbee used Sasuke as an excuse to flee from Raikage's supervision, so he pretended to be captured.
Source: episode 143 in the anime.
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