#1 Randy Orton vs the Undertaker - 2005
Termed as “The Legend Killer” back in his debut days, Randy Orton started a feud with The Undertaker when he landed an RKO on SmackDown after The Undertaker had beat World Tag Team Champions, Big show and Kane out of the ring.
The Viper arrived out of nowhere and put The Deadman down. But The Phenom rose up and the two would start a street-side brawl before Orton crushed the Undertaker backstage with a car.
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Justifying his title of “Legend Killer’, Randy Orton would come down to battle Matt Hardy on the next episode of SmackDown. After defeating him, the arena suddenly went dark as the voice of The Undertaker emerged from the dark.
Randy and his father, Cowboy Bob Orton Jr., tried to escape from the arena through various exits, but each time, The Undertaker prevented them from doing so. The Deadman finally showed mercy to Orton by challenging him to a Hell in a Cell match at SummerSlam.