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Picking the winner beforehand can make or break a Royal Rumble event. The winners often get a mixed reaction but other times, the victors are outright booed by the fans in attendance.
Some years, like in 1999 when Mr. McMahon won, featured stars who weren't real threats to win. There are also times when WWE nails the winners, like in 2019 (Seth Rollins, Becky Lynch) and last year (Cody Rhodes, Rhea Ripley).
Over the years, however, there have been some questionable calls by WWE for the booked winners. Batista's win in 2014 was met with a negative reaction, yet it ultimately led to the Yes! Movement and the rise of Daniel Bryan.
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The following five superstars shouldn't have won their respective Royal Rumble matches. The reasons why they shouldn't have won include better choices in the field at the time or losing in their title match at WrestleMania.
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#5 Mr. McMahon won the 1999 Royal Rumble
The main options to win in 1999 were Triple H, Stone Cold, Mankind, the Undertaker, and the Rock. Mankind and The Rock had their infamous 'I Quit' match on the same card, so they were out of the running.
Before the event, McMahon pitted Austin and the Undertaker against each other with only the winner earning a spot in the Rumble. The way things were handled made the match awkward as the only angle that mattered was McMahon/Austin.
Austin ended up getting the title shot anyway when McMahon forfeited his championship shot the next night. He primarily won because Stone Cold couldn't win three Rumbles in a row.
#4 Charlotte Flair was victorious in 2020
Charlotte Flair won the 2020 Royal Rumble before the COVID-19 lockdown. Her victory turned into an awkward situation as she had feuded with the then-champions, Bayley and Becky Lynch, many times prior to WrestleMania.
WWE opted for her to face Rhea Ripley as Ripley was coming off a huge NXT title win over an unstoppable Shayna Baszler. Just as with Asuka, Flair beat Ripley and quelled her momentum.
Baszler had eight eliminations and was the runner-up. The win could have presented her as a serious threat. Instead, she bit Becky Lynch and lost to her at The Show of Shows. Flair held the NXT title for two months and didn't do much to elevate the belt.
#3 The Rock couldn't help Roman Reigns in 2015
During the 2015 Royal Rumble, The Big Dog entered 19th and won the match, much to the chagrin of the WWE Universe. Even an impromptu appearance from The Rock couldn't save Reigns from the chorus of boos.
The main issue was that the early fan favorite, Daniel Bryan, was eliminated in the first half of the match after a 10-minute run. Bray Wyatt lasted nearly 50 minutes but was also eliminated before the final four.
Bryan's elimination only angered the fans, especially as other top faces like Dean Ambrose and Dolph Ziggler were easily dispatched by Kane and the Big Show. The crowd could see Reigns' win coming from a mile away, so they even started to cheer for the heel Rusev when he and Reigns were the final two.
#2 Brock Lesnar and #1 Ronda Rousey both won in 2022
The 2022 Royal Rumble winners - Brock Lesnar and Ronda Rousey - were two of the most disappointing winners in WWE history. Rousey returned to WWE after giving birth. She entered 28th and last eliminated Charlotte Flair, then the SmackDown Women's Champ, to win the match.
Rousey challenged her at WrestleMania instead of Becky Lynch (who was the RAW Women's Champ at the time). The Man and The Baddest Woman on the Planet never went one-on-one because Rousey chose The Queen. Flair would topple Rousey at The Show of Shows but lose to her at the next event.
Lesnar winning was a case of hotshotting the WWE Championship in 2022. He lost the belt to Bobby Lashley on the same card but was the final entrant in the men's Royal Rumble. Once his music hit, his win was inevitable. At WrestleMania, The Beast lost to Roman Reigns as Reigns unified the two titles.
