A few things that leap out to me here, on either side.
Andre's had wayyy more losses than a lot seem to know; El Canek, Jerry Lawler, Ron Garvin, Killer Kowalski, Harley Race, Antonio Inoki, Don Leo Jonathan, Lou Thesz, Karl Gotch, Strong Kobayashi, The Sheik, Hogan, Warrior multiple times. Even if we scratch the Hogan/Warrior ones, that's not an undefeatable monster. A guy with a very good win/loss for his role, yes. But one that didn't face the main eventers THAT often, with his share of losses when he did.
Secondly; assuming this is prime Vs prime, HHH is working heel and Andre is working face. All agreed? I think you'd struggle to claim that WM3 Andre was his peak despite it being the most exposure he ever gained. So question to the field - has Andre EVER lost to a heel as a face? EVER? All I see is him working heel and losing in the twilight of his career, and him losing face vs face matches usually in his opponents territories. I genuinely don't know the answer to this, maybe someone can help.
Third - I'm getting entirely fed up of this "HHH has never faced a guy like Andre" stuff. There hasn't been anyone in the history of professional wrestling as similar to Andre as The Big Show is, whom HHH has excelled against. Both are 500lb, 7 foot tall, stiff and athletic big men (Wight not so much now but Andre slowed down too). Is Andre better than Big Show? Of course he is. Kayfabe better easily, a far bigger draw and a better worker. But would you say "HHH has never faced a guy as hardcore as Terry Funk" if he had good experience vs Foley? Funk is more hardcore, Foley represents the same enigma. Would you say "he's never faced a guy as stiff as Billington" if he had shined against Benoit? "Never faced someone as manipulative as Flair" if he had handled Edge? You get my point.
So this kinda balances out for me. HHH should be considered one of the greatest ever in kayfabe, even if you dislike him or his politicking in the early 2000s. Those caliber of opponents, Andre has lost to. Plus, HHH has shown he's adept against the type of wrestler he's facing here. However, whenever I imagine this tournament and Andre's run, I see him falling to a HUGE face. Someone like Sammartino, Hogan, Cena. Therefore, I think I'm taking Andre to advance.
It's close though.