The connecting record
shownNaruto · ch. 49
Orochimaru beat Naruto Uzumaki in Naruto.
A seal shuts off the fox's chakra and Naruto is thrown aside, out of the fight.
What each of them is ranked on
The winner · 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
Beaten · Naruto Uzumaki · rank 5
The Seventh Hokage — shippuden
Inside Baryon Mode he outfights the strongest thing the sequel has produced, and the argument for fifth rather than first is what that costs: the form burns his own life to run, expires on a clock, and leaves somebody else to strike last. He also spent the entire series formally ranked genin — the lowest grade the system issues — and then became Hokage, the top of the same ladder, without passing the examination in between.
shownBoruto: Naruto Next Generations · Isshiki arc
Enters Baryon Mode and outfights Isshiki at the cost of his own lifespan. — 2021
statedNaruto · Konoha Crush arc
His promotion ceremony is interrupted and never rescheduled. — 2002
shownNaruto · Kaguya arc
Fights Kaguya alongside Sasuke in Six Paths Sage Mode. — 2014
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.