The connecting record
shownNaruto · ch. 345–346
Sasuke Uchiha beat Orochimaru in Naruto.
The body-transfer is turned around inside Orochimaru's own technique and Sasuke absorbs him.
What each of them is ranked on
The winner · Sasuke Uchiha · rank 6
shippuden
The other half of every fight in the tier above him, and the half that brings the tools rather than the volume — the Rinnegan lets him move between the same dimensions Kaguya uses to escape, which is what turns those fights from unwinnable into merely desperate. Carries the identical paperwork problem to Naruto: never promoted past the entry grade, having left the village before any retest could happen.
shownNaruto · Fourth Shinobi World War arc
Fights Madara with the Rinnegan and a complete Susanoo. — 2014
shownBoruto: Naruto Next Generations · Momoshiki arc
Fights Momoshiki alongside Naruto. — 2016
Beaten · Orochimaru · rank 10
classic · shippuden
Graded 35 of 40, half a point off the top, with an on-page record of losing — to Hiruzen at a cost, to Itachi immediately, to Sasuke from the inside. What keeps him this high is that none of the defeats stuck: the man's actual technique is not winning fights but declining to stay dead, and he is still present and operating long after most of the names above him are gone.
statedNaruto Databook 3 · 2008
Rated 35 of a possible 40.
shownNaruto · Konoha Crush arc
Fights Hiruzen Sarutobi and survives at the cost of his arms. — 2001
What this does not settle
One fight in one work. It is the only result the record gives between these two, and it is evidence about that meeting and nothing wider — not a general matchup, not a rematch, and not a ranking of its own.
The ladder above it is argued from everything either of them has been shown doing; this page is argued from one citation.
Where the two disagree, the disagreement is the point, and it stays visible rather than being resolved by whichever of them happens to be on this page.