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In the aftermath of this week's episode of Monday Night RAW, it was confirmed that Randy Orton will once again challenge for the WWE Championship at the SummerSlam 2020 pay-per-view, as 'The Viper' is set to clash against Drew McIntyre.
Over the years, Randy Orton has been a vital component at SummerSlam and since competing in his first pay-per-view in 2003, the 13-time WWE World Champion has been a marquee player at The Biggest Party of the Summer.
The year after his SummerSlam debut, Orton was rewarded for his incredible showing in WWE and headlined the 2004 SummerSlam pay-per-view where 'The Legend Killer' beat Chris Benoit in the main event to win the WWE World Heavyweight Championship.
Since then, a lot has changed in WWE and Randy Orton himself has been elevated from the tag of "prospect" to the status of "veteran" in WWE. And despite being in his 40s, 'The Viper' continues to be a vital part of the company and will once again have the opportunity to win the WWE Title this year.
Heading into SummerSlam 2020, it is safe to say that Randy Orton will be the heavy favorite to walk out as the new WWE Champion, especially considering his track record at The Biggest Party of the Summer.
Throughout the years, Orton has challenged for the WWE Title on multiple occasions at the SummerSlam pay-per-view, and in this article, I've listed the 5 different occasions when Randy Orton challenged for the WWE Championship at the SummerSlam PPV.
#5. Randy Orton vs Daniel Bryan - SummerSlam 2013
The SummerSlam 2013 pay-per-view will arguably go down as one of the most exciting SummerSlam pay-per-views of all time. The card was stacked from start to finish as the WWE Universe at the Staples Center witnessed a classic between Brock Lesnar and CM Punk, and a huge main event match between John Cena and Daniel Bryan.
By the end of the main event, it was Daniel Bryan who beat John Cena clean in the middle of the ring, won the WWE Title, and that too after Triple H counted the pinfall. With the WWE Universe going bonkers - confetti, and fireworks going off for good measure, it seemed like the supposed "B+ Player" finally had his moment in WWE.
But his celebrations were cut short, as the Money in the Bank briefcase winner, Randy Orton, made his way out to the ring and teased a cash-in, only for Triple H to hit Bryan with the Pedigree which led to 'The Viper' cashing in his briefcase and winning the WWE Title.
Randy Orton's win once again proved why he is considered as one of the most cold-hearted WWE Superstars of all time as he added further heartbreak to the WWE Universe, and another World Title reign to his long list of accomplishments.
#4. Randy Orton vs Sheamus - SummerSlam 2010
SummerSlam 2010 is memorable for all the wrong reasons *Team Cena vs Nexus-tsk, tsk* but the rest of the card was filled with solid singles (and a Handicap) matches.
In the third last match of the night, Randy Orton challenged then-arch rival Sheamus for the WWE Championship, however, the match didn't exactly live up to its expectations. Regardless of it, this still could be considered as one of Orton and Sheamus' best SummerSlam performances of all time, solely based on the final 4-5 minutes of the match.
Their in-ring styles are very similar to one another and their style of pacing led to a very slow match, least in the early stages of this match. In the final minutes of the match, the two exchanged their finishing moves and also dodged them as well. But once again, after all that build-up, the match ended via DQ and resulted in Orton winning the match but not the WWE Title.
Post-match, 'The Viper' hit Sheamus with a low-blow and an RKO on the table to at least get some momentum on his side.
#3. Randy Orton vs John Cena - SummerSlam 2007
Randy Orton and John Cena have had quite a rivalry over the years in WWE. Looking back a decade ago, the two veterans were the biggest rivals in WWE and faced each other on numerous occasions on WWE TV as well.
However, it wasn't until SummerSlam 2007 that Cena and Orton had their first singles match against each other on pay-per-view and this one sure did live up to all the expectations.
Heading into the match, John Cena was the babyface WWE Champion, whereas, Randy Orton, as always, was the hated heel who wanted to get his hands on the WWE Championship once again.
The match itself was a solid main event despite the slow start to it. The first half saw the two men mostly exchanging headlocks against one another but things eventually heated up in the second half of the bout. Much like every other Cena-Orton match, the ending of this one was built-up in a massive way and, eventually, the champ put away 'The Viper' to retain the WWE Championship.
#2. Randy Orton vs Kofi Kingston - SummerSlam 2019
Randy Orton is no stranger to challenging for the WWE Championship at SummerSlam. The last time he did so was last year when he and Kofi Kingston re-visited their rivalry from a decade ago and that led to a highly-awaited clash between the arch-rivals.
Orton and Kingston weren't exactly the biggest rivals in WWE but if you ask me, their chemistry in 2009 was a lot more interesting compared to whatever they produced at last year's SummerSlam PPV.
The duo had a decent enough match but once again, at times, the match felt quite lazy. Randy Orton hit an initial RKO on Kingston but the latter got his foot on the rope to prevent the three-count. And Orton's attempt at the Punt Kick eventually allowed the champion to hit 'The Viper' with a Trouble in Paradise.
The conclusion, however, was brilliant as Orton took things to a next level and mocked Kingston's family at ringside, which prompted the WWE Champion to use a kendo stick to brutalize Randy Orton and eventually set up a rematch for the Clash of Champions PPV.
#1. Randy Orton vs John Cena - SummerSlam 2009
After their initial SummerSlam clash in 2007, Randy Orton and John Cena once again shared the ring at SummerSlam, two years later. This time around the pair faced each other in a bizarre yet interesting match - a match that restarted about four times before there was an eventual winner.
Orton being the slimy heel that he was (and still is), wanted to take the easy way out and shoved the referee in order to take the DQ loss and retain the WWE Title in the process. However, WWE Chairman Vince McMahon tweaked the rules and said that if Orton caused a DQ finish, he would end up losing the WWE Title.
The second restart occurred after Orton took the title and walked out, causing a count-out but Mr. McMahon once again added that he would still end up losing the title. Orton tried a pinfall finish with his legs on the ropes but the ref caught him red-handed, the next pinfall attempt was interrupted by a fan, and we still didn't have a clear winner. Imagine being John Cena at this point!
The match restarted one final time and Orton pulled off a marvelous RKO while Cena was between the ropes and eventually another RKO got the job done for 'The Viper'.
This was quite a unique Orton vs Cena match and definitely a lot different from headlocks and slow first-halves.
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