Did Sasuke Orochimaru Ever Fight Naruto In A Canon Battle?

Such a fun nitpick — I love how Naruto fandom asks the tiny details that spin entire conversations at 2 a.m. So let me untangle the phrasing first, because your question could mean two slightly different things: "Did Sasuke or Orochimaru ever fight Naruto in canon?" or "Did Sasuke while under Orochimaru’s influence ever fight Naruto?" Both directions are worth answering, and I’ll walk through them with the canon/manga lens (with a nod to anime-only stuff later).

Sasuke absolutely fought Naruto in canon — more than once, and in two big, emotionally charged canonical duels that define their rivalry. The first major canon showdown is at the end of Part I, the original clash at the Valley of the End when Sasuke decides to leave Konoha. That fight is raw, young, and fueled by betrayal, ambitions, and immature pride. The second huge canonical fight is at the very end of the whole saga (the Final Battle in 'Naruto'/'Naruto Shippuden'), where they meet again at the Valley of the End and fight to the point of mutual annihilation (yep, the arm-losing moment). Those two are the marquee, plot-defining canonical fights between Naruto and Sasuke. There are also smaller skirmishes and confrontations around the edges of the story, but the two Valley battles are the big ones you want to rewatch if you want the emotional core.

Orochimaru, on the other hand, is a different case. In strict manga canon, Orochimaru never has a full, serious one-on-one "let’s go all out" fight with Naruto like Sasuke does. Orochimaru’s main canonical fights are with the Third Hokage, Itachi, and various other important characters, and his role is more as an instigator and manipulator for much of the series. He certainly interacts with Naruto — there are scenes where they clash briefly or he shows up to observe, and the anime (fillers) gives you plenty of Orochimaru vs. Naruto moments that feel like fights but are non-canonical. So if someone says "Did Orochimaru fight Naruto?" the answer in terms of manga canon is basically no full-scale duel; the anime gives you extra content where they swap blows or test each other, but those aren’t part of the manga-based canon.

If you meant "Sasuke while tied to Orochimaru" — like Sasuke after taking the Curse Mark or after being Orochimaru’s student — yes, Naruto fights that version of Sasuke in canon. The early Valley of the End battle and the surrounding moments include Sasuke sporting the effects of Orochimaru’s influence (curse mark power and ideology) because Orochimaru had already started corrupting him. Later duels involve Sasuke’s grown form (with other power-ups) and are still canon fights with Naruto.

If you want a concrete viewing plan: rewatch the Part I Valley of the End fight and then the Final Battle in 'Naruto Shippuden' back-to-back. If you’re curious about Orochimaru vs. Naruto specifically, check out the anime filler episodes (treat them like bonus scenes) — they scratch that "what if they really went at it" itch. I still get goosebumps watching those two canonical fights; they’re messy, loud, and oddly tender in how they show two stubborn people refusing to accept each other’s endings.