The connecting record
shownNaruto · ch. 660–661
Madara Uchiha beat Naruto Uzumaki in Naruto.
The Outer Path statue's chains pull Kurama out of him; Naruto falls unconscious and others keep him alive.
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 · 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.