#8 Randy Orton vs The Undertaker: WrestleMania 21

The streak should have ended years ago!
In fact, it probably should have happened at WrestleMania 21 when The Undertaker took on Randy Orton, but WWE still decided to have The Undertaker go over in the end. While it was an understandable position given the fact that the streak was still one of the biggest box office draws for The Show of Shows, Orton still would have been the best candidate to end it.
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Of course, a lot of fans are probably not going to agree with that assessment, especially since Randy Orton was the overly cocky, legend killer at the time, but he was still a fast-rising star and was the best candidate in a long time to actually beat the streak. He was young, amazing in the ring and would be one of the company's golden boys for a long time.
Unfortunately for Randy Orton, fate had a strange way of working out and The Undertaker ended up keeping his streak going for another nine years. Again, WWE probably made the right decision from a box office standpoint, but the future of WWE would have been a lot more interesting if Orton had beaten Undertaker at WrestleMania 21.
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