After defeating Batista the next night on Raw in a #1 Contenders match,Orton was unsuccessful in his attempt to win back the World Heavyweight Championship from Triple H at the 2005 Royal Rumble on January 30, 2005. After Batista's push began, Orton was marginalized. He began an onscreen relationship with Stacy Keibler and briefly feuded with Christian. After "Superstar" Billy Graham advised Orton to "go where no wrestler has gone before", Orton challenged veteran SmackDown! wrestler The Undertaker to a match at WrestleMania 21, making the ambitious claim that he would defeat The Undertaker, thus ending Undertaker's undefeated WrestleMania streak.
This feud saw Orton hitting the RKO on Jake Roberts, who had warned him about facing The Undertaker. Only two weeks before WrestleMania, Orton cemented his heel status by knocking Stacy Keibler out with the RKO; ending their on-screen angle. He went on to slap The Undertaker and assault him following a distraction by his father, Cowboy Bob Orton. Despite interference from his father, Orton was defeated by The Undertaker at WrestleMania 21 after he attempted a Tombstone Piledriver, but was off-balance, enabling The Undertaker to reverse the move into his own Tombstone Piledriver for the pinfall victory.
In storyline terms, a match with Batista on the night following WrestleMania aggravated Orton's shoulder problems stemming from the previous night (in actuality he was sidelined for several months while recuperating from his third genuine shoulder injury). While injured, Orton appeared on the May 16, 2005, episode of RAW, declaring his intention to gain revenge on Batista by defeating him for the World Heavyweight Championship. Orton claimed that he could not be drafted to SmackDown! as a result of his injury, but was informed by Vince McMahon that he was in fact an eligible candidate for the draft.
Orton returned to WWE television on the June 16, 2005 episode of SmackDown!, attacking The Undertaker and announcing that he was the second SmackDown! pick in the 2005 draft lottery. He made his in-ring return on August 11, 2005, fighting Kamala to a draw. Orton went on to defeat The Undertaker at SummerSlam following a distraction from his father, the returning Cowboy Bob Orton, who was disguised as a fan. After SummerSlam, an overconfident Orton announced on the first episode of Friday Night SmackDown! that he was opening a retirement fund for The Undertaker. However, The Undertaker made his return by setting the over sized check ablaze with a mysterious bolt of lightning. Orton began to become a full heel as fans started to dislike him as Bob Orton, Jr. began to help him win more matches, as it looked as if Orton were to lose matches against opponents like Hardcore Holly and Rey Mysterio.
After losing to The Undertaker on an episode of SmackDown!, Orton and The Undertaker began taunting each other using caskets. This led to Orton and his father facing The Undertaker in a handicap casket match at No Mercy 2005. The Ortons defeated The Undertaker after Bob Orton blinded The Undertaker with foam from a fire extinguisher, enabling his son to strike him with a chair. After sealing The Undertaker in the casket, Orton set the casket on fire and struck it with an axe.
At Survivor Series, Orton took Eddie Guerrero's place on "Team SmackDown!". Orton became the sole survivor of his team for a third time, pinning HBK to win the match for "Team SmackDown!". As Orton celebrated following the match, The Undertaker made his return, chasing Orton from the ring and indiscriminately attacking several other members of the SmackDown! roster.
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