6 times Bray Wyatt lost when he should have won
#5 Chris Jericho (Battleground 2014)
Chris Jericho is a legend in professional wrestling. Over a decade ago, he was able to garner an agreement with WWE that allowed him to essentially come and go as he pleased. In 2013, Jericho returned to the ring after a nearly six-month hiatus. He spent the majority of his six-month comeback tour that year as a stepping stone for some younger Superstars.
He lost to Fandango (in Fandango's first official match) at WrestleMania 29. Jericho had a one-off big match where he was essentially just a body to lose to a returning CM Punk in Chicago. He failed to win the Intercontinental Championship while feuding with guys like Wade Barrett, Curtis Axel, and Ryback. In the end, a loss to Axel and an attack by Ryback ended his return period. He would be gone for nearly a year.
In the middle of 2014, Jericho unexpectedly returned. He was immediately attacked by The Wyatt Family. Jericho and Wyatt would have a one-on-one match 3 weeks later at Battleground -- and Wyatt... lost?
Wyatt needed a big win after losing two out of three matches to John Cena. The first of those three matches was his first pinfall loss since his debut eight months prior. Chris Jericho would be the perfect rebound, or so he thought. Even with attempted help from Harper and Rowan, The Eater Of Worlds was unable to defeat Jericho and took his second pinfall loss since joining WWE.
He would go on to defeat Y2J at SummerSlam a few weeks later and again in a steel cage match on an episode of RAW. Wyatt was able to use those two wins to bounce back, and he would finish 2014 by defeating Dean Ambrose in four straight matches between the end of November into the very beginning of January.
That strong period for Wyatt is what makes the loss to Jericho so odd. If he was going to return to being unbeatable after a brief hiccup against John Cena, why start his return to dominance with a loss to an expendable opponent?