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5 biggest upsets in Monday Night RAW history

Lana got a big upset win on RAW.
Lana got a big upset win on RAW.

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.


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

John Cena lost to Britney Spears' ex-husband.
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.

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