Isamu Alva Dyson from Macross Plus in a YF-19 vs Maniac from Wing Commander in an F-95 Morningstar.
(or the same two guys, even if I’m not allowed to choose weapons/vehicles)
Leonardo the ninja turtle vs Mike Tyson
Taj Mahal vs Angkor Wat
Mr. Darcy vs Simon Belmont
Dr. Lydgate vs Dr. Mario
Gizmo from Gremlins vs Biollante
A baby dressed in a Gizmo from Gremlins costume vs Gamera
Paul Cézanne vs Henri Cartier-Bresson