5 biggest upsets in Monday Night RAW history

Monday Night RAW is the longest-running weekly episodic series on television in the United States. For 27 years, WWE has made RAW the company's flagship show, and we've seen many iconic moments, be it triumph or heartbreak.

While upsets can be rare on RAW, there have been some big ones. After the 14th December episode, let's take a look at some of the all-time upsets on WWE's flagship brand.

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#5. John Cena vs. Kevin Federline - RAW, January 1st, 2007

John Cena lost to Britney Spears' ex-husband.

John Cena vs. Kevin Federline was an odd match to see on RAW, even back then. John Cena had lost to Booker T in Cyber Sunday 2006 after Britney Spears' ex-husband Kevin Federline cost him the match.

It ultimately set up a John Cena vs. Kevin Federline bout on RAW, one that saw a massive upset. John Cena was a year-and-a-half into his run as the face of RAW and WWE in general, so it was a big shock to see the outcome.

Of course, the result on RAW only took place because of interferences from John Morrison and the late, great Umaga, but it was a big upset nonetheless.

The match on RAW was nothing great, and Jim Ross stated on his podcast that he although he didn't think much of the match, Kevin Federline did better than expected:

"Not much, quite frankly. The K-Fed thing was set up for he and [John] Cena to have a match on New Year’s Day. RAW that year was on January 1 and we were in Miami……it wasn’t like calling Rock and Stone Cold, I’ll tell you that. My hats off to John Cena for going along with it, pulling it out of the bottom of the ninth type deal, making it something. I guess K-Fed did a little better than some of us perceived he might. The K-Fed dates and the target being January 1 – Vince’s idea was its counterprogramming. All the football is gonna be on and we’re gonna counterprogram it. I don’t know how the ratings were on January 1, but nonetheless, Vince’s idea was to counterprogram football with sports entertainment."

Given John Cena's position at the time on RAW, he could have easily refused to lose to a non-wrestler. But to his credit, he went with it. Not many stars at his level could say the same.

It was one of the biggest upsets in the history of Monday Night RAW.

#4. Umaga vs. Santino Marella - RAW, April 16th, 2007

The Milan Miracle.

In what has been described as The Milan Miracle, Santino Marella defeated Umaga in his in-ring debut on RAW to become the Intercontinental Champion. When you make your RAW debut and win one of the most prestigious prizes in the wrestling industry, that is a moment to remember.

It was two weeks after the Battle of the Billionaires match at WrestleMania 23, where Bobby Lashley (representing Donald Trump) defeated Umaga (representing Vince McMahon). Umaga was the Intercontinental Champion at the time, and RAW went to Milan, Italy. Vince McMahon decided to ask a fan to challenge Umaga for the Intercontinental Championship in a No Disqualification match. Santino Marella was chosen as the fan, planted to make his debut.

While Santino Marella was getting squashed, Bobby Lashley's interference ensured that he would win the Intercontinental Championship on his RAW debut. It was a moment of magic and a great way for Marella to make his debut.

It was one of the big upsets in RAW history, especially considering how highly-touted Umaga was at the time.

#3. Shelton Benjamin vs. Triple H - RAW, March 29th, 2004

Shelton Benjamin and Triple H.

If there was any time for WWE to capitalize on Shelton Benjamin, it was when he was drafted to RAW. He spent time between 2002 to 2004 with Charlie Haas as a part of the World's Greatest Tag Team, and after getting drafted to RAW, he was all on his own.

RAW was dominated by Triple H and Evolution at the time. And two weeks after the iconic WrestleMania 20, the young upstart Shelton Benjamin would make his big RAW debut against The Cerebral Assasin.

In what would become the upset of the year on RAW, the young Shelton Benjamin defeated Triple H. It was the first of three times that he would get one over The Game, with the other two being via count-out and disqualification. It even led to him briefly feuding with Evolution, where he defeated Ric Flair and lost to Randy Orton in an attempt to become the Intercontinental Champion.

It was a big push to get for Shelton Benjamin, but ultimately, it didn't materialize in the long run. One can only be left to wonder what could have been with Shelton Benjamin on RAW.

#2. Lana vs. Nia Jax - RAW, December 14th, 2020

Lana pulled off a big upset victory over Nia Jax.

The most recent one on this list of RAW upsets saw Lana defeat Nia Jax in a match that nobody expected her to win. It was an enjoyable story where Lana, who isn't so experienced in the ring, teamed up with the RAW Women's Champion Asuka - a seasoned veteran.

The story saw the unlikely duo constantly pull off victories over Women's Tag Team Champions Nia Jax and Shayna Baszler. While they were winning, it was clear that Asuka was doing more, while Lana contributed in whatever way she could.

She took on Nia Jax on RAW on December 14th in a match that nobody other than Asuka expected her to win. In what was a clever finish, Lana would kick Nia Jax's legs while she was standing on the turnbuckles and used the awkward position to win with a pin from the top.

Given where both women are in their careers, it's safe to say that Lana's victory over Nia Jax was one of the biggest upsets in RAW history.

#1. Scott Hall vs. The 1-2-3 Kid - RAW, May 17th, 1993

An iconic moment.

All the matches on RAW that have been mentioned in this article were great upsets. However, when talking about the greatest upset in the history of Monday Night RAW, look no further than May 17th, 1993, when the established Razor Ramon was defeated by The Kid.

At the time, The Kid was a young 21-year-old named Sean Waltman, who would later go by the name of X-Pac. He made his RAW debut on May 3rd as The Kamikaze Kid but was unsuccessful against Doink The Clown. He took on Scott Hall, who was already an established WWE Superstar.

While it looked like it would be a typical squash match to make Razor Ramon look good, The Kid shocked the wrestling world with one moonsault, pinning Ramon by fluke and scoring a huge upset on RAW. In doing so, he earned the nickname 1-2-3 Kid.

It's one of RAW's early iconic moments. While 1993 wasn't a great year for WWE programming by any means, 1-2-3 Kid's win over Razor Ramon remains the greatest upset in RAW history.