Who Won the 1999 Royal Rumble? A Look Back at WWE History

Who Won the 1999 Royal Rumble? A Look Back at WWE History


By: HD Stock Images
May 2, 2025
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Welcome, wrestling fans! Today, we’re diving headfirst into one of the most electrifying events in WWE history—the 1999 Royal Rumble. This event not only marked the beginning of a new year in wrestling but also set the stage for WrestleMania 15. With unforgettable moments, surprise entrants, and an epic showdown, the 1999 Royal Rumble delivered some serious entertainment. Let's break down what went down that January night and analyze its lasting impact on the WWE landscape!

Background of the 1999 Royal Rumble Event

WATCH Vince McMahons shock Royal Rumble win in 1999  WWE News  Sky

The 1999 Royal Rumble took place on January 24 at the 18,000-seat Arrowhead Pond in Anaheim, California. This was the twelfth annual Royal Rumble event and was a pivotal moment in WWE history, closely tied to the ongoing rivalry between the promotion and WCW, as well as the rise of WWE's Attitude Era. Let’s take a closer look at the buildup to this event.

Leading up to the Rumble, the WWE was thriving thanks to its shift towards a more mature and edgy product. Characters were becoming more defined, storylines were intertwining seamlessly, and fans were fully invested in the action. Tension was at an all-time high, particularly between The Rock, Stone Cold Steve Austin, and Vince McMahon. Each of these figures played a crucial role leading up to the Royal Rumble.

Key Storylines Leading Up to the Event:

  • The Rock vs. Vince McMahon: The Rock, fresh off his rise as a main event star, had a heavily contested relationship with Vince McMahon. The tension was palpable, with McMahon attempting to manipulate the outcome of the Rumble in favor of his plans.
  • Stone Cold's Quest: Steve Austin, the rebellious favorite, was looking to reclaim his spot at the top of the card. The 1999 Rumble would be crucial for him to assert dominance ahead of WrestleMania.
  • Surprise Entrants: Speculation was rife about surprise entrants that could shake things up. Would legends return? Would unexpected faces appear? This anticipation added excitement to the build-up.

In the weeks leading up to the Rumble, the WWE did an excellent job of hyping the event. Weekly episodes of Raw and SmackDown featured intense promos, confrontations, and matches that made fans eager for the Rumble. The stakes were high, with the ultimate prize being a championship match at WrestleMania 15. This added another layer of intensity to the match, as superstars grappled not only for bragging rights but also for a chance at glory.

As the day approached, WWE fans worldwide were buzzing with predictions and discussions about who would emerge victorious. The anticipation was not only about the Royal Rumble match itself but also about how it would shape the Road to WrestleMania. The 1999 Royal Rumble was positioned to be a game-changer in many ways.

Now, let’s get into the dramatic moments and gripping action of the match itself, where things took some unexpected turns and led to one of the most controversial finishes in the history of the Royal Rumble. Stay tuned!

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3. Key Matches Leading to the Rumble

WWF Royal Rumble 1999  YouTube

As we gear up for the 1999 Royal Rumble, it’s essential to remember the key matches that paved the way for this explosive event. These bouts not only set the stage for the Rumble itself but also showcased the evolving storylines and rivalries that shaped WWE during that era.

First off, we can't overlook the December 1998 Armageddon pay-per-view. This event featured a spectacular main event that showcased the chaos and drama that fans had come to expect from WWE. The main event pitted Stone Cold Steve Austin against Vince McMahon in a no disqualification match. The heat between these two was palpable, and this match went a long way in building the enmity that would affect the Rumble. Austin's victory here further solidified his status as the top contender heading into the big match in January.

Another significant match to consider was the January 1999 episode of RAW is WAR. This episode was pivotal for several reasons. It included a heated confrontation between Austin and the returning Triple H, who would be making his presence felt in the Rumble. The tension was electric, and the buildup added layers to what fans would expect at the Rumble. It also allowed other superstars to position themselves as contenders, creating a fascinating dynamic as the date approached.

Don’t forget about The Rock, who was also a key focal point leading to the Rumble. His rivalry with Austin not only intensified but also involved other notable matches, including title defenses and confrontations on weekly shows. The Rock was a growing force in WWE, and fans were eager to see where he’d fit into the Rumble picture.

  • Armageddon 1998: Austin vs. McMahon – An explosive setup.
  • RAW is WAR (January 4, 1999): Triple H's return and Austin's confrontations.
  • Various Title Matches: The Rock defending his title added intrigue.

These matches and storylines interwove to create a rich tapestry of anticipation as fans eagerly counted down the days to the Royal Rumble. Not only were the stakes high, but the excitement surrounding the superstars involved set the stage for an unforgettable night.

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4. Highlights of the 1999 Royal Rumble Match

The 1999 Royal Rumble match itself was nothing short of a historical spectacle, filled with surprising moments, drama, and, of course, some unforgettable eliminations. Let’s dive into the highlights that made this event stand out.

First eliminated: The match kicked off with Creative Control members, Rue and Gerard, and even before the clock hit two minutes, the atmosphere was tense. The early action allowed fans to see who would stake their claim early.

Stone Cold Steve Austin: As the clock ticked, everyone knew Austin would come in at some point, and when he did—let's just say the crowd explosion was worth the wait! Austin entered as a fan favorite, and the crowd erupted as he leveled opponents left and right, reminding everyone why he was a top contender.

The Rumble isn't just about the last man standing; it's also about memorable moments. Kane made a significant impact in this year’s match, showcasing his dominance by eliminating multiple competitors in a short time. His size and power naturally placed him as a considerable threat to everyone involved.

CompetitorEliminated By
Stone Cold Steve AustinKane
KaneStone Cold Steve Austin
The RockStone Cold Steve Austin

The irony of Austin eliminating Kane, who previously terrorized him, was a twist that fans loved. As the match progressed, the usual chaos unfolded: alliances formed, renewed rivalries emerged, and moments of pure entertainment unfolded, with comedic spots and serious confrontations alike.

In the end, the highlight of the 1999 Rumble was undoubtedly the finish, where Stone Cold Steve Austin emerged victorious after a thrilling showdown, securing his place in history for that year. He beat The Rock, securing his spot at the main event of WrestleMania—what a journey it was!

Overall, the 1999 Royal Rumble was a blend of chaos, excitement, and unexpected turns, solidifying its place as one of wrestling's greatest events. The journey toward WrestleMania was well underway, and fans couldn't wait to see what was next.

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5. Who Won the 1999 Royal Rumble?

The 1999 Royal Rumble was a pivotal event in WWE history, and it was not just because of the intense matches and thrilling storylines leading up to it. The winner of this particular Royal Rumble match was none other than *Vince McMahon, the owner of WWE himself! Talk about a curveball! Vince's victory was unexpected and certainly raised eyebrows among fans and wrestlers alike.

Set at the spectacular Compaq Center in San Jose, California, on January 24, 1999, the match featured 30 participants, but the drama unfolded in a way that no one could have predicted. Throughout the match, Vince and his opponent, Stone Cold Steve Austin, engaged in a bitter rivalry, and their feud took center stage during the event. Austin, known for his rebellious persona, was in the thick of the action, poised to potentially win the match when chaos erupted.

As the match progressed, the interference from various characters added fuel to the fire. The Road Dogg, D'Lo Brown, and other superstars entered the fray, providing fans with classic wrestling entertainment. However, it was when Stone Cold Steve Austin was eliminated spectacularly – only to later return and create further chaos – that the match truly became unforgettable. Vince's sly tactics, utilizing the help of other wrestlers and underhanded strategies, ultimately led to his shocking win.

This victory marked the first time a non-wrestler won the Royal Rumble match, shattering the mold of who could possibly hold the title. Many fans were left scratching their heads, while others delighted in the unpredictable storytelling that WWE was known for. So, there you have it: Vince McMahon, with all his savvy and cunning, stood tall as the 1999 Royal Rumble winner, further solidifying his character's role as a key antagonist in the 'Attitude Era' storyline.

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6. Impact of the 1999 Royal Rumble on WWE History

The 1999 Royal Rumble didn't just set the stage for Vince McMahon's controversial victory; it became a landmark moment in WWE's evolution during the Attitude Era. This event was instrumental in shaping the future storylines, rivalries, and overall direction of the company. Let’s take a closer look at its impact:

  • Character Development: The match further developed the ongoing feud between Vince McMahon and Stone Cold Steve Austin, which would reach its climax at WrestleMania later that year. The dynamic between an anti-establishment hero and the corrupt authority figure became a staple, influencing storylines for years to come.
  • Storytelling Innovation: Winning the match as a non-wrestler was a bold narrative choice. It signaled that WWE was willing to break traditional wrestling norms, paving the way for unique story arcs and character developments that engaged audiences on various emotional levels.
  • Celebrity Involvement: The event featured appearances from celebrities like Jimmy Kimmel and Todd Pettengill*, emphasizing WWE’s growing interest in crossover appeal with mainstream culture and entertainment. This strategy opened doors for more celebrity appearances in the future, expanding WWE's reach beyond the wrestling world.
  • Evolution of Royal Rumble Format: The unpredictable nature of McMahon's win led to discussions about the Royal Rumble format itself, prompting future events to take more chances creatively, including unexpected entrants and surprise twists in storytelling.
  • Rise of the Attitude Era: This event is often credited with helping to solidify the WWE's “Attitude Era,” where characters became more complex and storylines darker. It’s a period known for its edginess and willingness to challenge the status quo in sports entertainment.

In reflection, the 1999 Royal Rumble was much more than just a wrestling match; it marked a significant turning point in WWE history, influencing both immediate and long-term storytelling and character development strategies. Its impact is still felt today, as WWE continues to push boundaries and entertain fans worldwide.

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7. Legacy of the Winner: Career Highlights

When we think about the 1999 Royal Rumble Winner, we have to talk about the incredible legacy left by this wrestling superstar. The winner, known for his charisma and unmatched athletic ability, didn't just capture the Rumble glory; he launched a career that would inspire millions of fans worldwide. With a knack for captivating storylines and unforgettable performances, he quickly became a household name in the WWE.

Over the years, the winner collected numerous championships, including:

  • Multiple WWE Championships
  • Intercontinental Championship reigns
  • Tag Team Championship titles
  • A Royal Rumble victory in another year

Each of these achievements marked a significant milestone in his career. However, it was his ability to engage with the audience that truly set him apart. From his electrifying promos to high-stakes matches, he had a unique way of connecting with fans. His larger-than-life persona helped to elevate the sport, making wrestling more than just entertainment; it became an art form.

Another remarkable aspect of his legacy was his influence on future generations of wrestlers. Many current WWE superstars cite him as a major inspiration. They emulate his work ethic and dedication to the craft, demonstrating that passing the torch is an essential part of wrestling culture. Moreover, his contributions to wrestling extended outside the ring. After his wrestling career, he became a successful actor, using his platform to reach new audiences and bridge the gap between sports and entertainment.

In summary, the legacy of the 1999 Royal Rumble winner is rich with accomplishments, both on and off the mat. He is a testament to the idea that hard work and passion can lead to greatness. His presence in wrestling is felt even today, as countless fans continue to celebrate his contributions to this beloved sport.

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8. Fan Reactions and Historical Significance

The 1999 Royal Rumble and its dramatic conclusion did not just leave an impression on the fans present that night; the echo of this event still resonates within the wrestling community today. The winner's triumphant moment elicited a range of reactions, from sheer joy to intense debate, showcasing the passionate nature of wrestling fans. Whether you were in the arena or watching from home, the energy was electric.

Fans were divided; while many celebrated the victor's win as a defining moment in wrestling history, others expressed concerns about the booking decisions leading up to the Rumble. This dichotomy sparked countless discussions online and during fan gatherings, proving the engagement wrestling can incite. It wasn't simply about who won; it was about how the story unfolded.

The winner's impact also extended beyond the Rumble itself. This match played a crucial role in establishing a new era for WWE. Following its conclusion, the winner would participate in high-profile feuds and main event storylines that transformed the company and attracted a broader audience. The storyline twists and turns kept fans on the edge of their seats, making them emotionally invested like never before.

Interestingly, the 1999 Royal Rumble served as a watershed moment in WWE's history. It coincided with the Monday Night Wars, a period when WWE faced significant competition from WCW. The excitement surrounding this Royal Rumble event helped shift public perception and brought a fresh resurgence to WWE's popularity. Its significance can't be understated, as it contributed significantly to the evolution of wrestling entertainment.

In conclusion, the reactions from fans and the historical significance of the 1999 Royal Rumble winner highlight just how pivotal this moment was in wrestling history. Whether loved or debated, the event and its star have left an indelible mark on the sport, ensuring that generations to come will remember the excitement and fervor of that unforgettable night.

Conclusion and Final Thoughts on the 1999 Royal Rumble

The 1999 Royal Rumble was a pivotal moment in WWE history, marking a significant transition in the attitude and direction of professional wrestling. With Vince McMahon emerging as the unexpected winner, the event set the stage for a turbulent and exciting path for WWE. This landmark event wasn't just another pay-per-view; it played a crucial role in building the narrative for the upcoming WrestleMania, providing fans with unforgettable moments and storylines.

While the controversies surrounding the match, including the treatment of various superstars and the chaotic nature of the finish, raised eyebrows, they also highlighted the shift towards a more unpredictable and dramatic wrestling style that would define the Attitude Era. Key takeaways from the event include:

  • Impactful storytelling: The Rumble established stories that continued to unfold in the weeks and months that followed.
  • Character development: Superstars like Stone Cold Steve Austin and The Rock solidified their status as fan favorites.
  • Innovative booking: Vince McMahon's victory demonstrated the potential of non-traditional winners, challenging the norm.
  • Memorable moments: The match produced iconic scenes that fans still cherish today.

In conclusion, the 1999 Royal Rumble was not only a noteworthy pay-per-view event but also a significant chapter in WWE's storied history. It marked the beginning of a new era, showcasing how unpredictable outcomes could capture audience attention and change the landscape of professional wrestling forever.

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