10 pay-per-view matches Triple H Should Have lost

#5 Triple H vs Randy Orton- Unforgiven 2004

Even bigger momentum killer

Randy Orton was WWE's hand-picked face of the company as early as 2003. He was given a major boost as a member of Triple H's Evolution stable and was one of the best performers on RAW throughout 2003 and 2004. Then the plan came to have him shoot up the ladder on his own, and things got a little messy. Orton captured the World Title at SummerSlam 2004, much earlier than planned. Allegedly the plan was for Orton to win the 2005 Royal Rumble and basically be the Batista of that Triple H vs Batista feud. However, Orton was getting more popular every week, which likely contributed to the alleged change of plans.

In a memorable segment, Evolution turned on Orton on the post-SummerSlam RAW and began his face run, and it would almost immediately go crashing down. Triple H would surprisingly defeat Randy for the World Championship at Unforgiven, ending the Legend Killer's reign at just 28 days. The loss killed almost all of Orton's momentum instantly. Fans just seemed to have lost interest after this and Orton would lose to Triple H two more times on pay-per-view before his planned redemption at WrestleMania 21.

It would be 3 years later before Orton would be a World Champion in WWE again, this time trading victories with Triple H in several Championships pay-per-views over the next 2 years.