Home / Highway to Hell in a Cell / Highway to Hell in a Cell: The Undertaker vs. Randy Orton – Armageddon 2005

Highway to Hell in a Cell: The Undertaker vs. Randy Orton – Armageddon 2005

We continue The Highway to Hell in a Cell with a look at the culmination of a feud that captivated the WWE Universe for nearly a year. The “Legend Killer” Randy Orton was being built-up to a major WrestleMania moment as he was put in one of the main attractions at WrestleMania 21 against The Undertaker.

What we didn’t know at the time is that this WrestleMania clash would culminate in a bloody Hell in a Cell match at Armageddon 2005.

Going into WrestleMania 21, many believed that Randy Orton would in fact be the man to beat The Undertaker and conquer The Streak. Even 10 years ago, people were predicting that The Undertaker’s retirement would be imminent. The Undertaker proved everyone wrong as he looked as good as ever in his series of matches with Orton.

Undertaker-Randy-Orton-Hell-in-a-Cell-2The WrestleMania 21 build featured cameos by wrestling legends including ‘Superstar’ Billy Graham encouraging Randy Orton to “go where no man has gone before” at WrestleMania. Jake “The Snake” Roberts also appeared on Raw for the first time in many years warning Randy Orton to be careful against The Undertaker at WrestleMania…and getting an RKO in return.

We also saw Randy Orton turn heel on his then-girlfriend Stacy Keibler in an infamous moment where he laid her out with an RKO in the middle of the ring. Randy also received help from his father, ‘Cowboy’ Bob Orton in this feud. However, The Undertaker emerged victorious at WrestleMania. Unfortunately for The Deadman, this wasn’t the last time he heard from Randy Orton.

Both men went their separate ways for a while and in June 2005, Orton was drafted to the Smackdown brand. This was the perfect recipe to book a rematch between the two competitors at SummerSlam. Heading into SummerSlam, Orton bragged that he wanted retribution and he was finally going to “kill the legend” of The Undertaker.

These two has a stellar match at SummerSlam 2005, which is vastly underrated compared to their higher profile WrestleMania 21 match. Both men hit their signature moves throughout the contest until a fan jumped into the ring to distract Undertaker. This gave Orton the opportunity to hit the RKO and win the match.

The mysterious fan who jumped into the ring? ‘Cowboy’ Bob Orton.

An immediate rematch was booked on a following Smackdown where The Undertaker once again defeated Randy Orton, but not without mind games coming from The Ortons. During the contest, Bob Orton drove a U-Haul truck to ringside & emptied a casket to the floor. When Undertaker approached the casket & tried to put Randy into it, he noticed there was a mannequin of himself. This was done to set up the 4th match in this series at No Mercy 2005 where Undertaker would take on The Ortons in a casket match.

orton-taker-casketThe Undertaker had to put both Ortons into the casket to win, but couldn’t overcome the odds as the use of a fire extinguisher & a chairshot to the skull allowed enough time for Randy to lock Undertaker inside the casket.

What transpired afterwards was something that has been done to Undertaker time & time again: the casket was set on fire!

Shortly after, a backstage vignette was played where The Ortons opened the brunt up casket to find nothing inside.

However, The Undertaker disappeared from Smackdown for a while, which he had tended to do over the course of his run. Heading into Survivor Series 2005, Orton was one of the major players on the Smackdown Survivor Series Team against the Raw Team. During the elimination match, Orton was able to secure the victory and become the sole survivor.

After the match, the Smackdown Team came out of celebrate with Orton when a casket emerged erected vertically. A lightning bolt struck the casket and set it on fire as The Undertaker returned. He cleaned house of the Smackdown superstars, but The Ortons were able to escape. The was the perfect set-up for a colossal Hell in a Cell match to finish the feud at Armageddon 2005.

Wrestling fans, this is how a feud should be built a culminated. Randy Orton & The Undertaker had a series of high profile matches, each meaning something significant, heading into Armageddon and their main event conclusion. A match that started out in the middle of the card on all previous Pay-Per-Views was now the main event.

This match was everything we thought it would be. Randy Orton had shown how “hardcore” he could get in his Backlash 2004 battle with Mick Foley. This one didn’t disappoint. It wasn’t long into the match when The Undertaker introduced a steel chair and cracked Orton over the head twice in a row, cutting him from ear to ear. The blood was pouring. Randy regained control when he hit an ‘out of nowhere’ RKO across the top rope, knocking The Undertaker off the apron and into the cell.


Before you know it, the steel steps were introduced as both men successfully struck each other with them. Randy then got retribution on The Undertaker as he cracked him over the head with a steel chair, cutting Taker wide open.

Somewhere along the course of the match, ‘Cowboy’ Bob Orton got involved and was slammed into the cage by The Undertaker, cutting him open as well. This was controversial after the fact because it was later found out that Bob Orton had Hepatitis C during this match. He allegedly told Executive Vice President of Talent Relations John Laurinaitis this, but Big Johnny let Orton get cut open by Undertaker anyway! (Undertaker left WWE television once again out of protest of this transpiring. He was pissed and rightfully so!)


Randy Orton held onto control of the match and put Undertaker through a table. Referee Nick Patrick was knocked silly & the cell had to be opened to let him out, a tactic that has been used several times in Hell in a Cell matches. Undertaker regained control and hit the last ride on Randy. This allowed for ‘Cowboy’ Bob to enter the cell and help his son by pulling the second referee out of the ring and knocking him out!

A lot of back & fourth went down, including Orton hitting a tombstone on The Undertaker with Taker sitting up out of the pin! Randy tried to put Undertaker down over & over again with straight right hands, but Taker kept sitting up! Undertaker started to make his comeback. ‘Cowboy’ Bob reentered the match with The Undertaker’s urn, but was unsuccessful. Undertaker ended up using the urn to his advantage, hitting both Ortons with it and then hitting them both with tombstone piledrivers, pinning Randy and winning the match.


The Undertaker ascended to the top of the cell & celebrated in his own unique way with the WWE fans. This was the end of their rivalry and helped Orton add an amazing body of work to his resume. Both men went on to have significant years in 2006 and beyond. The Hell in a Cell match has been a staple of The Undertaker’s career & culminating his rivalries, which he will do with Brock Lesnar on October 25, 2015 at WWE Hell in a Cell.

Randy Orton went on to compete in numerous Hell in a Cell matches as well against the likes of John Cena, Sheamus, Mark Henry  Daniel Bryan. Orton slowed down his “Legend Killer” schtick after his loss to The Undertaker, but still brought it back from time to time when he faced other legends.

The Undertaker was one of the few legends that Randy Orton wasn’t able to defeat.

About Jay Alletto

Jay Alletto is the owner of PWPNation.com! He’s interviewed many notable names in pro wrestling including: ‘Superstar’ Billy Graham, Lex Luger, Diamond Dallas Page, Maria Kanellis & more.