Winner: Muhammad Ali by unanimous decision
But Andre never faced anyone quite like Rocky. Both guys had heart, but Rocky's was bigger. I don't see Rocky giving in and staying on the floor in a fight against Raymond Bishop the way Andre did. I dunno. This would be a fast-paced war of attrition that Andre would not be prepared for. I see Andre doing OK against Rocky in the early rounds, but once Rocky finds his rhythm, Andre would be unable to keep Rocky off of him and would take a beating, leading to a late round stoppage. I imagine this fight would be similar to Rocky's fights with Archie Moore and Ezzard Charles.
Winner: Rocky Marciano by TKO during the late rounds
Joe would sometimes end things early if his opponent hurt him (Tony Galento, Max Baer) or if he viewed him as a threat - (Max Schmeling, John Henry Lewis, Buddy Baer, etc). Given Andre's reputation for winning fights with a broken hand, knocking out Isaac Frost, I believe Louis would see him as a threat and not waste time once the bell rings.
Once The Brown Bomber hurts Andre with his first significant punch, it would be the beginning of the end. That's when Louis would put his finishing blows together and put Andre to sleep. Andre can't out-slug Louis nor can he out-box him. Andre may get a good lick in here or there, but this fight only lasts as long as Joe wants it to.
Winner: Joe Louis by Knockout
But I feel that Andre could be smart enough to pull off a victory here. Lewis had a habit of abandoning his jab when guys repeatedly hit him in the body. (See his battle with Ray Mercer and his rematch with Holyfield for references). If he employs a constant body attack early on, Andre would be able to manipulate Lennox into a close-range brawl, which works to Andre's advantage. It's possible that maybe he'd counter Lewis and sneak something past him to get a knockout, but most likely he'd win a close decision in a toe to toe war. If old Holyfield and Ray Mercer could nearly push Lewis to the brink by forcing him into a shoot-out, then I think Andre has a real chance here.
Winner: Andre Bishop by decision, but it could just as easily go the other way.
Like Marciano, Frazier does not tire. So any hope of wearing Frazier down for a late stoppage is futile. Andre doesn't have the big punch of a George Foreman to stop Joe, and he's not built for a nose-to-nose 15 round slugfest with him either. Joe works him over with big hooks and body attacks, eventually stopping him with a thunderous left hook. Andre would be too battered and beaten to continue.
Winner : Joe Frazier by late TKO
Winner: Larry Holmes by unanimous decision
But on the other foot, Andre has a puncher's chance against Johnson, who had a suspect chin. I think Johnson would slap Andre silly for the most part, but Andre has a puncher's chance and had a history of outsmarting some of this opponents. Would it work against Johnson? I'm not sure. Johnson might just be too tricky for Andre. But in a 12-15 round fight, Andre would find a way to set up the big punch he needs.
Winner: Andre Bishop by knockout
Winner: Evander Holyfield by TKO during the late rounds.
To make it short, the Klitschkos would beat Andre. They were a little too patient for Andre to find anything to play off of. While Isaac Frost was similar in size to the Klitschkos, he fought a predictable and stupid fight, trying to blast Andre out of the ring during the early rounds. The Klitschkos would bide their time and counter. With a lack of punches to counter and play off, Andre wouldn't be able to bring anything to the dance. He would be on the outside of their long jabs all night. Andre could attempt to work them over with body shots, a'la Isaac Frost, but the Klitschkos wear their trunks up so high that he might get disqualified for "hitting low." There's just too much against Andre in a battle with these guys. He loses by decision or maybe a knockout if the Klitschkos decide to later in the fight.
I realize that Wlad and Vitali are two different fighters and fans of theirs may be offended that I grouped them together. After all, Vitali is a more awkward fighter, but has the better chin and is more comfortable in a slugfest if the opportunity arises. Wlad, on the other hand, is more of the classic boxer-puncher type. He arguably hits harder than his brother, but doesn't take a punch as well and avoids aggressive encounters as much as possible. But to save time here, the Klitschkos would beat Andre the same way, which is why I put them together in this list.
Winners: The Klitschkos by Unanimous Decision or late TKO
George Foreman, Sonny Liston, Max Baer, Jack Dempsey and Mike Tyson
Max Baer had better stamina than Liston and Foreman, but his crude haymakers would leave him open for counters from Andre.
Tyson and Dempsey were smaller than Baer, Liston and Foreman, but they were at their best during the early rounds. Andre was smart enough to avoid getting caught up during their early blitz and would take them apart when they slow down after round 4 or 5.
Winner: Andre Bishop by late knockout