The connecting record
statedNaruto · ch. 601
Madara Uchiha beat Tsunade Senju in Naruto.
Decided off the page, by a Madara still reanimated but free of Kabuto's control. The Kage are found near death and Tsunade cut in two once he has moved on to the main battlefield.
What each of them is ranked on
The winner · Madara Uchiha · rank 4
shippuden
Five Kage at once, then the allied army, then the two protagonists together — the war arc keeps escalating what it puts in front of him and he keeps going through it. The only reason he is not first is that he is removed from the story by betrayal rather than by any of it, which is a statement about Kaguya and not about the people who could not stop him.
shownNaruto · Fourth Shinobi World War arc
Fights the assembled Five Kage simultaneously and defeats them. — 2013
shownNaruto · Fourth Shinobi World War arc
Becomes the Ten-Tails jinchuriki and engages the allied forces. — 2014
Beaten · 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
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.