#4 Kurt Angle vs John Cena - WrestleMania 36
Kurt Angle ended his career with a loss to Baron Corbin at WrestleMania 35. But things might have turned out differently had Kurt Angle gotten his way. Angle had wanted to lose to John Cena on his way out. While Angle was in a program with Corbin at the time, Angle wanted Cena as he wanted to retire.
Vince McMahon told the WWE Legend that he could have John Cena at WrestleMania 36, but Angle felt that he couldn't go another year. He said:
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He said, ‘If you want John Cena you got it. But this year you got Baron.’ I said, ‘Vince, I’m not going next year. I’m done, this is it.’ And he said, ‘Well, you’re stuck with this.'
It makes sense why the WWE Hall of Famer wanted John Cena. Cena made his TV debut on WWE SmackDown in 2002 and challenged Angle. In a sense, Angle's career would have come full circle if he had lost to Cena, who started his WWE career facing him.
One thing is for sure -- the WWE Universe would have loved this proposed story and the sheer history of the match and it would have brought the house down. But alas, it remains only a dream.
#3 Sting vs. The Undertaker
Sting vs. The Undertaker can be best described as the one that got away. Sting had been tempted multiple times over the years with a match against The Undertaker, but it never happened.
Part of the reason why Sting didn't come to WWE till 2014 was because he was concerned about how WWE would use his character. At WrestleMania 33, Sting did face Triple H, but the Undertaker match never came to pass. Part of the problem was that father time had caught up with both men.
Sting was 55 when he made his WWE debut, and The Undertaker was not far behind either. In an interview, The Undertaker said that it wouldn't meet the expectations that had been set. He said:
"But where I kind of differ from a lot of people is I look past the marquee value and I look on the ability to deliver. So like you said, there's so many people that are clamoring for that match that I just don't know that the match could deliver on the people's expectations."
Perhaps if Sting had come to WWE right after WCW was purchased, history might have been different. At this point, it's highly doubtful that the pair will ever actually compete in the squared circle.