The connecting record
shownNaruto · ch. 170–171
Tsunade Senju beat Orochimaru in Naruto.
Jiraiya fights beside her. Orochimaru, whose arms are already sealed and who has Kabuto with him, is knocked down and retreats with Kabuto.
What each of them is ranked on
The winner · Tsunade Senju · rank 11
The Fifth Hokage — shippuden
The same 35 as Orochimaru and an entirely different shape of career, which is the most useful comparison the scorecard accidentally sets up. Her seal converts stored effort into recovery fast enough that ordinary damage stops being a limit, and she holds a village together through an invasion that removes most of its leadership. Equal numbers, opposite records, and the number does not distinguish them.
statedNaruto Databook 3 · 2008
Rated 35 of a possible 40, level with Orochimaru.
shownNaruto · Pain's Assault arc
Sustains a village-wide barrier and healing effort until collapse. — 2009
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.