Naruto Fights pein (or pain) in Naruto Shippuden Episode 163 with the title “Explosion! sage mode“.
Released June 02, 2010
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Sensing trouble, Naruto and Fukasaku asked to get summoned from Mount Myoboku to the Leaf Village. Upon arriving it was hard for Naruto to recognize that it was his village that he was standing in. This was because Pain/Pein had damage the village almost beyond recognition a few moments before Naruto arrived. Arriving in sage mode, naruto was able to sense that his teacher kakashi had died. Feeling extremely sad and angry naruto then engages Pain/Pein in battle.