6. The Ultimate Warrior
Possible WrestleManias where both were on the WWF Roster:
WrestleMania VII, WrestleMania VIII, WrestleMania 12.
The Best WrestleMania for that Match to happen: WrestleMania VIII
While The Undertaker was still new to the World Wrestling Federation in spring of 1991, when WrestleMania happened, The Ultimate Warrior was in a hot feud with the Macho Man Randy Savage, so this would not have been the time and the place for these 2 larger than Life Superstars to wrestle each other.
They did have a couple of Live Event Matches later that year, with The Ultimate Warrior getting the win every time. The next year would have been perfect though, that is if 2 things hadn’t actually happened. 1st, in order to have a classic Babyface vs. Heel Match, it should have been avoided to turn The Undertaker Babyface in February of 1992. And 2nd, The Ultimate Warrior shouldn’t have held Vince McMahon up for some bonus money right before the SummerSlam 1991 PPV, which of course resulted in him getting fired the second the PPV was over.
He did return after the Main Event of WrestleMania 8, but in order to to the Warrior vs. Undertaker match, he would have had to be back way before the big PPV.
Let’s say the match actually happened and The Undertaker went over, it would have certainly meant more than him beating Jake The Snake Roberts … nothing against Jake, he’s great, but at this point The Ultimate Warrior was a much bigger star than him.
