I am quite the fan of crazy/obscure match stipulations. I in fact designed some ideas that eventually grew out into some other feds that I feel as if have always been rather obscure. In fact I have a examples. 
When I think of match stipulations I find that the one fun match to modify is the Iron Man match. Why? Because there's so much you can do with a simple Iron Man stipulation. Two of my favorite include a "Scramble" style Iron Man match. Where instead of being the one to get the most falls to win, you have to be the one with the last fall in order to win. 
Another being what I call a "Steeltown Table Match" where it's basically an iron man match in which falls are set by putting your opponent through tables. Then there's my more complicated one I call a "Pure Endurance Match" basically taking the ROH Pure Championship rules, putting them into an Iron Man match and have your ropebreaks reset by taking a fall. 
Basically for everything Vince Russo has put on a pole in the crappy era of WCW, I have modified a concept as big as an iron man match. 
Other than that my more elaborate ideas was a Ragnarok Match. Basically a Multi Man Gauntlet Match contested inside a steel cage with ECW level Hardcore weapons involved. 

Though I take keen interest in looking at the crazy matches people have thought up of and how exactly do they work. Feel free to post them. Especially since House of Glass seems to have a theme for Glass Style deathmatches.

Hell in a Cell Inferno Pillow Fight Bra and Panties Match.
right, @Cailin Dillon ?

坂崎ハルナ wrote:

Hell in a Cell Inferno Pillow Fight Bra and Panties Match.
right, @Cailin Dillon ?

Next week's Empire Main Event confirmed!

Nastradamus wrote:

坂崎ハルナ wrote:

Hell in a Cell Inferno Pillow Fight Bra and Panties Match.
right, @Cailin Dillon ?

Next week's Empire Main Event confirmed!

Oh Schmidt's about to get real. $10 CAD says one of the pillows catch fire

Nastradamus wrote:

坂崎ハルナ wrote:

Hell in a Cell Inferno Pillow Fight Bra and Panties Match.
right, @Cailin Dillon ?

Next week's Empire Main Event confirmed!

no, we'll save it until our title match at Road to Redemption. 

坂崎ハルナ wrote:

Nastradamus wrote:

坂崎ハルナ wrote:

Hell in a Cell Inferno Pillow Fight Bra and Panties Match.
right, @Cailin Dillon ?

Next week's Empire Main Event confirmed!

no, we'll save it until our title match at Road to Redemption. 

Doesn't matter. My bet still stands

Alright so, I thought of a match where a lethal weapon would be kept in the middle of the ring locked away by a key. That key will be suspended high above in the ring. Now the participants in that match has to grab that key, unlock the weapon and then beat their opponent so much that they won't be able to stand up for the 10 count.

Mike Showman wrote:

Alright so, I thought of a match where a lethal weapon would be kept in the middle of the ring locked away by a key. That key will be suspended high above in the ring. Now the participants in that match has to grab that key, unlock the weapon and then beat their opponent so much that they won't be able to stand up for the 10 count.

So kinda like Saw?

KellyHackenschmidt wrote:

Mike Showman wrote:

Alright so, I thought of a match where a lethal weapon would be kept in the middle of the ring locked away by a key. That key will be suspended high above in the ring. Now the participants in that match has to grab that key, unlock the weapon and then beat their opponent so much that they won't be able to stand up for the 10 count.

So kinda like Saw?

Well people actually won't die in this match lol

Mike Showman wrote:

KellyHackenschmidt wrote:

Mike Showman wrote:

Alright so, I thought of a match where a lethal weapon would be kept in the middle of the ring locked away by a key. That key will be suspended high above in the ring. Now the participants in that match has to grab that key, unlock the weapon and then beat their opponent so much that they won't be able to stand up for the 10 count.

So kinda like Saw?

Well people actually won't die in this match lol

Yeah. Figured. Lol

Walker Lumberjack Match.

I use to have this match idea where before a match happens, criteria are randomized and its a list of 3 goals that must be done in order to win the match. It can range from use this move, make your opponent submit, bleed, whatever, and it basically was no rules other than, you gotta do these 3 things in order to win the match.

I have done this match once, but I feel like it has a lot of room to improve in terms of potential. I recall the rules I had made in the first version of this match was Checklist 1, Use a finisher of your opponent, Checklist 2, make them bleed, and Checklist 3, make them submit. And it was something like if you didn't do them in order, like you made them tap before they bled, it doesn't count, but I feel like matches like this are made in mind with special referees as well as making tasks insanely difficult and random. 

It's no DQ, no count outs, can happen anywhere as long as an official sees the task getting completed, and it takes a bit of strategy to pull off. Never could figure out a good name for it though.

Rotating Tag Team Partners.

Every so often the Tag Team partners switch clockwise, four teams, so the winner might be a combination that didn't even begin the match.

Barbed Wire Wrapped Exploding Rubber Chicken Match, it's exactly what it sounds like... my brother came up with it NOT me.

Spawned from us attending an IWA:Mid-South show and bringing weapons for a deathmatch... we wrapped a rubber chicken in barbedwire and Axl Rotten LOVED IT.

"Imitation Game Match"

Both competitors are forbidden to use their own sig/finishers and have to swap with their opponents.

Just like in the op I had a similar idea. Two teams of four or five (or three trios) competing under scrambled rules. The twist is that they are locked inside a hiac star le cage that has weapons attached to it and one section wrapped in barbwire. Recently house of glass inspired me that think of a glass ladder match and also a house of. Mirrors/bull in a China shop match where a set ofobjects made out of glass is set up and you have to beat your opponent all the way back to the ring for the pinfall or submission.

In the fed I owned and ran, I had a title that changed hands by being in a different person's possession for five referee counts. The first title match involved pretty much the whole roster, with weapons allowed, being outside the ring was allowed, and the title belt itself was placed in the center of the ring after being presented by XFL alumni (I called it the NWR-XFL Title; the match was based off the XFL's opening scramble). The goal was to grab the title, have the ref count to five, and get the hell out of dodge after the ref raised your hand, because as a 24/7 title, it was immediately up for grabs. The more I think about it, the less I think this was actually a match type and more of an excuse for me to write a giant clusterfuck of what the hell.

Some of mine are tame, if not e-fed cliche.  One was a Green House of Horror match, which was essentially a hell in a cell type structure with 9x9 panels of glass making up the walls and ceiling instead of steel mesh.  The catch was that some of the glass is the thick hockey rink stuff that doesn't give or break easily, thus making it just as brutal, if not more so, when you try to put your opponent through it with a high impact move. Another Hell in a Cell tropes I've fallen victim to is the Hell in a Cell lit on fire.  I think I called it the Towering Inferno.  The major threat in the match wasn't so much the fire that inexplicably engulfs the cell's frame, but also heats and weakens the mesh, making it prone to skin searing shrapnel.

There was also the "Roulette" or "Red Rover" Rumble, which I've explained elsewhere.  Four competitors surround ringside in a timed entry styled battle royal.  If someone's thrown out on their side, they get to take part in the match.  The following entrant takes up the empty space at ringside.  Here's the controversial storyline driving part though; People can be eliminated on empty sides of the ring, thus not allowing a new entrant from the outside.  If everyone's eliminated from the in-ring action while there's still opponents waiting on the outside to have someone thrown out on their side of the ring, then they're disqualified and the winner is the last man in the ring.  Sound's convoluted? A little, but if it happened in real life I think the constructs would be way more apparent than what comes from my incessant driveling.

I've also had a strange indy dream match that I kind of want to pitch to a local trash bag indy or $5 Wrestling, which is an Elimination Chamber match with six porta-john's as the chambers.  It's silly, and stupid, but I know people who'd love to be booked in silly and stupid shit that would do it for free.

Glass Wallz 

Methuselah wrote:

Glass Wallz 

That image is fucking beautiful.

A Tag-Team Handicapped Match 4 vs 2 in an Inferno Hell in a Cell

Methuselah wrote:

Glass Wallz 

Faarrrrkk that needs updating.

Anyway, never saw the light of day but Hangman's Asylum; Hell In A Cell cross Ultimate X. Bit smaller than the modern day structure, bigger than the original design, roof cut off and replaced with truss scaffolding.

I can't really say I thought of something so crazy that it never saw the light of day, but I guess you could say the No Way Out Match was kind of crazy. We've actually used it three times now, but it's essentially a large Hell In A Cell-sized structure made of prison bars instead of steel mesh, no turnbuckle pads, no mats, no door, and four smaller cells connected to chains that lower to the ground when each competitor in them joins the match. Also, we added fire to the walls of it when it started getting used at our fire-themed FPV, Dia Del Diablo.

Oh yeah, I guess you could also say one I wanted to do a while back was crazy. I called it the Crimson Mask Match, where both opponents bust themselves open prior to the match started and then fight until one passes out from damage/blood loss.