The Royal Rumble event is arguably the most optimistic and exciting time of the year for wrestling fans. WrestleMania season starting and the fan desire to dream of what’s to come carried the build. The Rumble match itself is an outstanding concept that will always create interest based on the combination of surprises, unpredictability and high stakes.
Even the non-Rumble matches on the PPV hold great importance at such a major event. Unfortunately, that doesn’t mean that every match or moment will make sense in the bigger picture. There have been some creative decisions that left a lot to be desired. Each of the following were the most questionable to come on the Royal Rumble stage.
10 Vince McMahon Winning The Royal Rumble In 1999

WWE took a huge risk by putting Vince McMahon into the ring and having him win one of the most important matches of the year. The McMahon vs Steve Austin feud was becoming too popular to deny, and it led to their first in-ring PPV match at the Royal Rumble 1999 event.
Both Austin and McMahon were the first two entrants that led to them brawling all over the venue, with The Corporation getting involved. The heated enemies returned to the ring in time to be the final two when Vince won after The Rock distracted Austin. WWE had Austin win the title shot back, but McMahon winning this match was extremely questionable.
9 Hulk Hogan Cheating Sid Out Of Rumble Match

One of the most controversial Royal Rumble moments came when Hulk Hogan got eliminated and refused to head back. Sid Vicious was an ally of Hogan before this match and shocked his friend by eliminating him in the legendary 1992 Rumble with the WWE Championship on the line.
However, it was every man for himself when Sid eliminated Hogan and became the only man remaining against Ric Flair. Hogan grabbed Sid and essentially helped Flair push him over for the win. This was an odd booking decision to make fans have reason to question Hogan for the first time.
8 Charlotte Flair Winning Rumble Over Shayna Baszler

WWE called up Shayna Baszler from NXT in the 2020 Royal Rumble match and a full-time spot on the Raw brand afterwards. The logical Rumble finish would have been Shayna winning since she was always planned to challenge Becky Lynch at WrestleMania 36.
However, WWE decided to go with a curveball by having Charlotte Flair win, despite not challenging the Raw or Smackdown Women’s Champion. Charlotte won to challenge Rhea Ripley for the NXT Women’s Championship since this was during the time WWE wanted NXT to compete with WWE.
7 Kurt Angle Vs Mark Henry Main Eventing Over Rumble Match

WWE had a strange main event choice at Royal Rumble 2006 when Kurt Angle vs Mark Henry closed the show. The Rumble match is usually the best option, and Rey Mysterio’s feel good win dedicating it to Eddie Guerrero may have been the perfect show closer.
Even the WWE Championship match between John Cena and Edge held greater importance. WWE questionably booked Angle beating Henry in the main event since it set up The Undertaker’s return. However, there were plenty of breaks for an older Undertaker to make his returns feel less special.
6 Diesel & Bret Hart Having A Draw During Diesel's First PPV Defense

WWE pulled off a huge title change when Kevin Nash’s Diesel persona won the WWE Championship from Bob Backlund. The title win came out of nowhere on a house show just days after Diesel turned face ditching Shawn Michaels.
Bret Hart being the first challenger to Diesel on a PPV at the Royal Rumble 1995 event was a risky move. WWE went with a cheap draw finish of both men being continuously attacked by various heels. Nash has admitted that he felt this hurt his title reign right from the start.
5 Forcing Batista's 2014 Rumble Win Over Obvious Daniel Bryan Story

One of the most controversial nights in Royal Rumble history featured the audience completely taking over the Rumble match in 2014. Batista returned from a long stint away from WWE and received a massive push from the start.
Fans started booing when Rey Mysterio was the 30th entrant and that confirmed that Daniel Bryan would not be in the match. The story was so easily there that WWE deserved the criticism for straying away from what the audience wanted until fixing plans after this match.
4 Booking The Entire 2015 Rumble For Roman Reigns Win

WWE humorously found themselves in the same problem one year later at the Royal Rumble 2015 event. Daniel Bryan was once again the fans choice when Roman Reigns had the win. However, the booking was an issue more than just the finish of booking Roman to win.
Reigns had the entire match built all around him with elimination after elimination. Even the ending story of Big Show and Kane stacking the odds against Roman was horrible thinking. Fans turned on the match to harm Reigns' push for years after this night.
3 Matt Hardy Betraying Jeff Hardy To End WWE Championship Reign

Jeff Hardy had a mystery attacker heading into his Royal Rumble 2009 WWE Championship defense against Edge. Rumors of Christian returning in this role had fans excited until WWE shifted gears at the last minute.
Matt Hardy was instead selected as the person attacking Jeff to cost his brother the WWE Championship. The idea of Matt helping Edge win gold was bad enough, but the feud against Jeff turned out to be a huge disappointment. Christian was clearly a better option to return in a major way rather than his wasted ECW return.
2 Sheamus Winning Rumble Match Over Chris Jericho

There have been many years of fans reacting negatively to wanting one name to win the Royal Rumble over WWE’s actual choice. Royal Rumble 2012 ended up being one of the better instances of the fans having a point.
Sheamus eliminated Chris Jericho as the final two to challenge Daniel Bryan for the World Championship. Jericho was the obvious other title contender to CM Punk and had returned with huge momentum. The win would have been a bigger moment for Jericho’s character rather than forcing Sheamus to deal with fan resentment.
1 Edge Dropping WWE Championship To John Cena For Transitional Reign

WWE did not expect Edge to have great momentum as WWE Champion when cashing in MITB on John Cena. The following PPV of the Royal Rumble 2006 event presented a difficult scenario of deciding who should win their title match.
Cena won since the WrestleMania 22 plan was always to have him face Triple H. However, Edge increasing ratings and creating buzz warranted retaining. WWE went with the original plan and made Edge a transitional champ. Edge thankfully rebounded when he got more title opportunities down the line to become a legend.
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