Naruto vs Pain started in Ep 163 & finished in Ep 174 of shippuuden & Ch-431 to Ch-449. Goku vs Freiza lasted a lot longer in episodes atleast but I don't know about manga chapters. Goku vs friza still wins, but not by much 306-325, thats 19, compared to narutos 18. wait gokus actually longer, it goes to and with 328, which is 3 more chapters which is then either 21 or 22 depending on how you count