Every Major Triple H Vs. Randy Orton Match, Ranked From Worst To Best

The rivalry between Triple H and Randy Orton was born when Triple H unceremoniously booted Orton out of Evolution, after he became the youngest World Heavyweight Champion at the age of 24 in August 2004. The Cerebral Assassin often found himself on the winning side of this rivalry.

Both men have a lot in common, they are multi-time World Champions and have even closed out WrestleMania together. Their rivalry resulted in some truly memorable, and some forgettable matches. Their epic battles often took centre stage on several pay-per-views, making this one of WWE's most influential rivalries of the last two decades.

13 One Night Stand 2008

For the second time in eight months, Randy Orton and Triple H squared off in a Last Man Standing Match for the WWE Championship. The Game defended the championship with Orton hell-bent on regaining the title at the final One Night Stand event in 2008.

Unfortunately, the Game threw Orton over the top rope, and he landed awkwardly, breaking his collarbone. The Viper was evidently in pain and was clutching his shoulder for the remainder of the match. Therefore the match was shorter than expected, as Orton was in no shape to compete.

12 No Mercy 2007 (Match #1)

Randy Orton kickstarted his first WWE Championship reign at No Mercy 2007 with John Cena relinquishing the title due to a pectoral injury. No Mercy was a historical night for the WWE Title with Orton defending the title against Triple H in an impromptu match.

Orton and the Game opened up the show with a decent match. Triple H ended up capturing his 11th World Championship by rolling up Orton for the victory. It was a surprising way to start the show with Orton invoking his rematch clause in the main event, there's more on that later.

11 Judgment Day 2008

Judgment Day 2008 pitted Triple H and Randy Orton in a steel cage match for The Game's newly won WWE Championship. Orton was chasing the title after Triple H captured his 12th world title at Backlash.

Orton tried to escape through the cage door when the bell sounded, which was a smart move but the Game quickly reeled Orton back into the ring. Nonetheless, Triple H avoided Orton's Punt by delivering a sickening chair shot to the challenger. The Game retained the title after nailing Orton with his patented Pedigree.

10 Super ShowDown 2019

The most recent high-profile clash between Triple H and Randy Orton occurred at Super ShowDown 2019. This match had no build and there was nothing at stake to boot.

Ultimately, the match was slow and methodical, which is typical for a Triple H style match. The Game was no longer at the peak of his powers, but it was a treat for the fans in Saudi Arabia to see two legends go head-to-head. Orton prevailed, which was a rare one-on-one victory over Triple H for him on PPV.

9 WrestleMania XXV

Main eventing WrestleMania is a huge privilege, but Orton and Triple H had the unenviable position of having to follow a five-star classic between Shawn Michaels and The Undertaker at WrestleMania XXV. The Viper was headlining WrestleMania for the first time after winning the 2009 Royal Rumble match.

Unfortunately, fans were disinterested in this affair, which hurt the bout. The Game retained the WWE Championship, although Orton should have gone over, as he was in a rich vein of form.

8 Unforgiven 2004

Randy Orton's destiny was fulfilled when he dethroned Chris Benoit at SummerSlam 2004 to capture the World Heavyweight Championship. However, Triple H was jealous and he viciously booted Orton out of Evolution.

The two had an underwhelming World Heavyweight Championship clash at Unforgiven, which was Orton's first PPV title defense. Orton was never suited to being a babyface and this was one of his worst world title reigns. Furthermore, lots of interference aided Triple H in capturing his ninth world championship, which was another controversial outcome, with Orton not holding a world title for another three years.

7 Backlash 2009

The WWE Championship was defended in unique circumstances at Backlash 2009. Triple H, Batista and, Shane McMahon took on Legacy in a six-man tag team match. However, there was an added caveat, if any member of Legacy pinned either Triple H, Batista, or Shane O'Mac, the Game would lose the WWE Title.

This was an extremely competitive match with The Game and Orton fighting backstage before both men made their way back to ringside. The Game kicked out of Orton's RKO, but that didn't prevent the Apex Predator reclaiming the WWE Championship from Triple H with a devastating Punt to the head.

6 Night Of Champions 2009

A WrestleMania rematch occurred at Night of Champions 2009. Randy Orton defended the WWE Championship against his biggest rivals, John Cena and Triple H, in a magnificent triple threat match.

The Game was drafted back to Raw in the draft lottery, and all three men stole the show in a brilliant encounter. However, Orton's lapdogs Rhodes and DiBiase got involved with Orton isolating with Cena, and picking up the huge win. It was a tainted win, but extremely impressive nonetheless.

5 The Bash 2009

The Bash 2009 was home to Triple H and Randy Orton's final one-on-one PPV match against each other for a decade. Orton's WWE Title was on the line in a Three Stages of Hell match.

Triple H got himself intentionally disqualified with the first fall being a standard single's match, by nailing Orton with a chair. However, he quickly leveled the scores in a Falls Count Anywhere match with a Pedigree on the floor. The Game was closing in on his 14th world title in a stretcher match but Legacy interfered, with Orton pummelling Triple H onto the stretcher and pushing it over the line.

4 Royal Rumble 2005

At the 2005 Royal Rumble, Raw General Manager Eric Bischoff announced that Triple H's World Heavyweight Title defense against Randy Orton will have Evolution barred from ringside.

This is an underrated match between the two, often forgotten due to their other matches taking precedence. Orton dominated most of the match until Triple H gained the upper hand. The Game targeted Orton's injured knee, as he continued to assert his dominance, walking into WrestleMania 21 with the title.

3 Backlash 2008

Randy Orton v Triple H v JBL v John Cena Backlash 2008 Cropped

Randy Orton was in the midst of a breakthrough six-month reign as WWE Champion, heading into his title defense at Backlash 2008. Orton defended the title against John Cena, JBL, and Triple H in a fatal 4-way elimination match.

This match captivated audiences from start to finish, who were heavily invested in this contest. Big Match John eliminated JBL with an STF, which allowed Orton to pounce on Cena with a Punt to eliminate him. Orton and Triple H battled it out for a solid 15 minutes with fans backing The Game. He kicked out of the RKO, and won the title with a Pedigree. Sadly for Orton, it was his third World Championship reign brought to a halt by Triple H.

2 WrestleMania XXIV

Randy Orton's WWE Championship reign was under serious jeopardy at WrestleMania XXIV when he defended the title against John Cena and Triple H in a stacked triple threat encounter.

All three men gave it their all on the Grandest Stage of Them All. However, Orton earned one of the biggest wins of his career by punting Triple H at the last second and pinning a prone Cena to become the first heel in years to retain the WWE Championship at WrestleMania.

1 No Mercy 2007 (Match #2)

Triple H stunned Randy Orton in the opening match of No Mercy 2007, leading to Orton invoking his rematch clause in a memorable Last Man Standing match in the main event.

This match encapsulates how great both Orton and Triple H can be, when they are motivated. It was a brutal encounter with Orton refusing to give up. Ultimately, Orton expertly countered The Game's Pedigree into a stunning RKO onto the announce table. Orton reclaimed the WWE Title in a historic night with three WWE Title changes at the same event.

NEXT: Randy Orton's 10 Best World Championship Matches Ranked