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Craziest Stipulations We’ve Seen at WWE Extreme Rules

| April 2, 2021 9:32 am PDT

The WWE Extreme Rules was launched as a standalone event in 2009 which makes it a relatively new show on the pro wrestling schedule.

And yet, the production already earned a loyal fanbase thanks to the wild matches throughout the years. The very concept behind Extreme Rules is to deliver extraordinary fights.

While some may have gone too far to the point of silliness, others certainly left a mark in WWE history. This post is focused on the latter, exploring the best Extreme Rules stipulations.

Before I move on to my selections, let me just clarify what made the cut. I’ve picked both one-off occasions that were simply too impressive to miss and stipulations used multiple times.

CM Punk vs. Chris Jericho Chicago Street Fight (2012)

The Chicago Street Fight stipulation has been used on several occasions by the WWE and it features the following rules.

  • No Disqualifications
  • No Count-Outs
  • Win by Pinfall or Submission Only

The terms are simple and you can easily understand what this one is about – an old-fashioned brawl with basically no rules.

You can hurt the opposition in any way imaginable and that’s why Chicago Street Fight deserves a place in my list of craziest WWE Extreme Rules stipulations.

The organization has used these terms on several occasions, but none showcases the beauty of the format better than the 2012 clash between CM Punk and Chris Jericho.

It was a wild fight that saw kendo sticks, fire extinguishers, and other weapons flying around. Check this one for yourself if you don’t believe me.

It’s the most exciting one for me, but there were other cools bouts under the same rules as the clash which saw Ahmed Johnson and Legion of Doom face the Nation of Domination at WrestleMania 13.

I’m sure that this format is going to be used in the future as well and I won’t be shocked if it happens at one of the next few Extreme Rules editions.   

Wyatt Swamp Fight, The Horror Show at Extreme Rules 2020

2020 was a tough year because of the health crisis and WWE was forced to improvise for many PPVs, including the Extreme Rules edition.

The company decided to launch a cinematic clash called Wyatt Swamp Fight between Braun Strowman and Bray Wyatt as the main event.

Some fans thought it was too cheesy, others loved it. The truth may be somewhere in the middle, but it was certainly an impressive experience and among the craziest Extreme Rules stipulations we’ve seen so far.

The gritty atmosphere and the special appearance of Alexa Bliss contributed to the match too.

The fight had plenty of twists and turns that ended with the rise of Wyatt’s old persona The Fiend.

It was a fun night and while the stipulation probably won’t be used ever again, it certainly deserves some praise in terms of creativity and atmosphere.

Dolph Ziggler vs. Seth Rollins Iron Man Match (2018)

The Iron Man stipulation was born way back in the 1990s and had a long history before the birth of WWE Extreme Rules.

I can’t leave it out of this list, though, especially since one of the most memorable fights under such rules came at the event in 2018.

Dolph Ziggler was back against the wall in this year’s Extreme Rules main event, but he fought back to defeat Seth Rollins in an epic fight for the WWE Intercontinental Championship.

It was a back-and-forth affair and that has been always the case with Iron Man matches.

The concept behind it is simple – there is a fixed limit of time, usually 30 or 60 minutes, and each wrestler attempts to record as many falls as possible. The one with the most when the time expires wins.

If the score is tied, an overtime under the sudden death rule may be requested and that’s has been the case in most situations when we had a draw.

The WWE has often used the Iron Man stipulation in the past and the fans certainly like it. Here’s a list of some of the most iconic bouts under these rules throughout the years.

  • Shawn Michaels 1-0 Bret Hart (1996)
  • Brock Lesnar 5-4 Kurt Angle (2003)
  • Chris Benoit 4-3 Triple H (2004)
  • John Cena 6-5 Randy Orton (2009)
  • Bayley 4-3 Sasha Banks (2015)

I expect to see more Iron Man Matches in the future and at least some of them are likely to be part of WWE Extreme Rules.

Dean Ambrose vs. Chris Jericho Asylum Match (2016)

The weapon-on-a-stick concept has seen many variations throughout the years. I could’ve easily added a different one here, but I believe that the Asylum Match between Dean Ambrose and Chris Jericho at Extreme Rules 2016 went the extra mile.

We had no idea how the clash would look like when Ambrose challenged his opponent during the build-up to the show.

Once Jericho accepted and the duo met in a cage, it was instantly obvious that it was going to be a fun night.

There were all sorts of weapons hanging above the wrestlers and most of them were used at one point of the fight.

Ambrose ultimately won this match and while it had some silly moments involving a mop, it was a feast for the fans and certainly added a new spin by combining the best of other popular Extreme Rules stipulations.

I’m not sure whether WWE will come back to the very same format in the future, but something similar should be part of the schedule sooner rather than later.


The best stipulations are not only fun, but they also open the door to some exciting WWE wagers. You can check our Extreme Rules betting guide for tips on how to find them.

In the meantime, feel free to add your own suggestions for the most entertaining rules applied at the show. I’m sure I might be missing some great matches and I would love to read about your favorite ones.

Jerry Summer

Jerry Summer has a wide-ranging interest in gambling and the gambling industry. He's made a living out of both playing poker and betting on sports.

The English Premier League and the NBA are among Jerry's primary areas of expertise. He's knowledgeable about many other sports, too, along with poker and several casino games.

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