Randy Orton has had a long and illustrious career in WWE that has included many great matches, in several different characters. He first debuted with WWE in 2002 and for nearly two decades has put together a legacy that will put him down as one of the greatest ever.

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Orton is best known as being one of the most dangerous heels in WWE history, but he has had several successful runs as a babyface as well. His best matches have come as both a heel and a babyface, which makes it very interesting to look back at his 5 best matches as each.

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10Babyface: Randy Orton Vs AJ Styles – SmackDown (March 7, 2017)

After several weeks of turmoil surrounding who would challenge Bray Wyatt for the WWE Championship at WrestleMania 33, Randy Orton and AJ Styles went to war on the March 7, 2017 episode of SmackDown to determine just that.

This is one of the most underrated matches of Orton’s career. He and Styles have amazing chemistry which resulted in an absolute classic. The Viper came away with the victory after hitting an RKO, but both of them came out of this looking fantastic.

9Heel: Randy Orton Vs John Cena – Bragging Rights (2009)

John Cena is the greatest rival of Randy Orton’s career. They have had many great matches together, with their best being at Bragging Rights 2009. This was their last match of a yearlong feud for the WWE Championship.

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This was a 60-minute Iron man match, which compliments Orton’s skill set perfectly. The ring psychology these two showed was off the charts, and Orton’s viciousness was at an all-time high. Cena came away with the victory, beating Orton 6-5.

8Babyface: Randy Orton Vs Christian – Over The Limit (2011)

When you are looking at Randy Orton’s best matches as a whole, you can’t overlook his showdowns with Christian. When you are looking at his best matches as a babyface, it’s impossible too. Their 2011 feud over the World Heavyweight Championship was one of Orton’s greatest and the matches they had were unforgettable.

Their first PPV clash was at Over The Limit 2011. This was a highly intense match where the storytelling was amazing. They went back and forth, both having counters for everything the other had. Christian gave it his all, but it was Orton who claimed the victory.

7Heel: Randy Orton Vs Batista Vs Daniel Bryan – WrestleMania 30

WrestleMania 30 was all about Daniel Bryan, but Orton was just as important on that night. In the main event, Orton defended his WWE World Heavyweight Championship against Batista and Daniel Bryan in a Triple Threat match.

This was an amazing match which included a lot of action and tons of drama. Orton played his role perfectly doing everything he could to take Bryan out of the equation. But there was magic was in the air and Bryan’s determination was just too much, which created an all-time great WrestleMania moment.

6Babyface: Elimination Chamber Match – New Years Revolution (2005)

At New Years Revolution 2005, Randy Orton was part of the third Elimination Chamber match ever, challenging for the World Heavyweight Championship. The other competitors in this match were Triple H, Batista, Edge, Chris Jericho, and Chris Benoit with Shawn Michaels as the special guest referee.

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This was an action-packed match where each competitor played a part in making it special. Orton played the role of the babyface perfectly, having to try to overcome both Batista and Triple H as the final three competitors. He was able to eliminate Batista, but it was Triple H who walked out with the title.

5Heel: Randy Orton Vs John Cena Vs Edge Vs Shawn Michaels – Backlash (2007)

This match was always going to be great. Four of the best that WWE had to offer, all in one match for the company’s top prize. Shawn Michaels, Edge, and Randy Orton challenged for John Cena’s WWE Title in a Fatal 4-Way match at Backlash 2007.

This is in the conversation for being the best Fatal 4-Way match in WWE history. It had breakneck action from start to finish and no fan could guess who might win. The finish was crazy with Cena retaining the title after pinning Orton.

4Babyface: Randy Orton Vs Seth Rollins – WrestleMania 31

At WrestleMania 31, Randy Orton took on Seth Rollins in a fantastic grudge match. This feud was built for months prior to this match, and when it finally culminated it was spectacular.

Orton’s and Rollins’ styles were a great mesh. This was a vicious battle which included a lot of physicality, and good technical wrestling. It looked like Rollins was closing in on the victory, but Orton hit him with what might’ve been his best RKO ever to win.

3Heel: Evolution Vs The Shield – Extreme Rules (2014)

After losing his WWE World Heavyweight Championship to Daniel Bryan at WrestleMania XXX, Orton was immediately inserted into a feud with The Shield. This culminated in a dream match between Orton, Triple H, and Batista of Evolution and The Shield at Extreme Rules 2014.

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This match was an instant classic. It started with a slow pace but then quickly erupted into utter chaos. It featured a lot of great spots, highlighted by Rollins’ dive from the stands, and ended with The Shield standing tall.

2Babyface: Randy Orton Vs Christian – SummerSlam (2011)

The last match of Randy Orton’s and Christian’s fantastic 2011 rivalry happened at SummerSlam 2011 when they faced off in a No Holds Barred match for the World Heavyweight Championship.

This was a match where both Orton and Christian were hell-bent on destroying each other. They both used whatever weapons they could get their hands-on and they did a great job in entertaining the crowd. In the end, it was The Viper who retained his title.

1Heel: Randy Orton Vs Cactus Jack – Backlash (2004)

At Backlash 2004, Randy Orton defended his Intercontinental Championship against Cactus Jack in a No Holds Barred match. This was arguably the most important match of Orton’s career because it truly turned him into a superstar.

This was an absolutely brutal affair that played to both Orton’s and Foley’s strengths. They beat each other down with all kinds of weapons and created many great spots. The Viper came away with the hard-fought victory after he delivered an RKO to Jack onto a barbed wire baseball bat.

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