Oh my God...so many.
The Chamber of Horrors (Halloween Havoc 91) = It is legendary in how stupid it was. It is like the "Batman & Robin" of Wrestling Matches. The point of the match is to strap someone to an electric chair and murder them and that isn't even the worst part of it.
The Concrete Crypt (Great American Bash 2004) = This one doesn't get nearly enough credit for being as awful as it is, but GOD! OK, so the whole point of the match is that if Undertaker doesn't laydown, Paul Heyman will murder Paul Bearer. Words can't describe how inane this entire thing was.
Doomsday Cage (Uncensored 96) = The structure itself looked like something you'd see on a Nickelodeon Game Show like Legends of the Hidden Temple. The real issue though was in the layout. So it is Hulk Hogan and Randy Savage Vs. 8-10 guys...and they still win. OK.
Kennel From Hell (Unforgiven 1999) = I feel like this came out of the mind of a 7 year old. It looks awesome on paper. Steel Cage PLUS Hell in a Cell PLUS Rabid Dogs! Huzzah! The problem though is that there was absolutely no way you could pull this off without it looking completely ridiculous, which it was. How on Earth are you going to get the dogs and act and behave the way you want for that long a period? It just wasn't possible.
Stairs Match (TLC 2014) = I thought Chairs match was really pushing it, but this was just the ultimate "We don't know what to do, so f it" gimmick match I think I've ever seen, and it didn't help that the match was terrible.
Brawl for All (WWF 1998-Wrestlemania XV) = This was another idea that sounds cool on paper, but is in no way practical in execution. How can a bunch of guys that have been trained to pretend to fight be expected to have actual shoot fights? It is ridiculous, stupid, and dangerous to the performers. Horrible idea. Some would throw some of the boxing matches up there, but some of those can at least be faked well enough with some bells and whistles to make it work. These were just awful, looked fake, and guys only got hurt and embarrassed from it.
Kendo Stick Match (Raw 98) = Nobody remembers this one, but it was a match between Steve Blackman and Daren Drozdov where the object was to basically sword fight with Kendo sticks and whoever dropped their stick first was the loser. Does it sound bad? Good, because it was.
Various Sexy Diva Matches (WWF/E 1999-2006) = I appreciate hot women as much as the next guy, but these type of matches became increasingly stupid. Pudding Matches. Swimming pool matches. Lingerie matches. Gravy bowl matches. Bikini matches. Pillowfights. Water balloon fights. It was like 12-13 year old boys were writing this. And yeah, we can blame Russo for starting it, but WWE kept doing it for years after he was gone. I mean, yeah the ladies looked good doing it, but there comes a point where it just looks trashy and stupid, and I'd rather see the women taken seriously as competitors, which they pretty much are now.
Lumberjack Matches (various) = I hate Lumberjack matches for the simple reason that it maintains the idea that all faces are on one side and all heels are on the other. Almost every LJ match I've ever seen boils down to both sides coming to blows, but if you think about it for 10 seconds, it makes no sense. Why would the babyfaces around the ring want to help the good guy? Why would the heels want to help the bad guy? What do they get out of it by helping him? It takes the complexity out of the characters and just renders the characters as interchangeable shells on one side of a coin.
Pole matches In General (Various) = People seem to be under the impression that Vince Russo invented the pole match, and that isn't true. Pole matches go away back. The earliest one I have seen happened in 1985. Russo sure did love to book them though as he booked alot of them. I think my main problem with them is that I would just rather see a Ladder match which is far more interesting and in matches where the idea is to say grab a weapon...what is the point of that? Why go to all that trouble, especially if the match is No DQ to begin with. And other ones are just used to be dumb like a Mexican Hat on a pole match (NOT Russo) or a Viagra on a Pole (yup, that was Vinnie Ru's)
Electrified Cage (Lockdown 2007) = Similar to other aboveexamples, yeah, it looks and sounds awesome on paper, but if you think about it for more than 5 seconds, you realize how impractical the whole idea is. Is there any way you can convey that the cage is electrified without either A) Being extremely dangerous or B) Being extremely hokey and fake. Fortunately, they went the hokey and fake route as I'd hate for The Dudleys and LAX to be put in danger over something this ludicrous.
Blacktie Brawl and Chain (Hard Justice 2008) = Oh yay, another TNA one. Somebody really needed to do a once over on this gimmick and tell the powers that be that it mechanically can not work. Come on Russo, you can't chain both men together AND put a tuxedo match gimmick on top of that. How are they going to rip each other's tuxes off (by the way, that gimmick was always stupid to me, but whatever) if they are chained together? That's just...dumb! It should be one or the other (preferably the chain match).
Luck of the Irish Match (TNA 2004) = Yay! Another TNA one. We're on a roll. This one slips between the cracks of stupid things that TNA did, but it might be the number one lamest gimmick match I have ever seen. So the match involved Pat Kenney (Simon Diamond) and Disco Inferno. The idea was that there were four foot lockers in the corners of the ring, one of them filled with weapons. Both men would fight over a football with a key attached to it (having fun yet?) and the key would enable them to open the footlockers and possibly find the weapons. Ironically, this was one where putting the boxes up on poles would have made it better! (seriously Vinnie Ru, the ONE time a match could use poles and you DON'T do it?!). I just sat there watching this the whole time screaming "Uh, why don't they just pick up the boxes and shake them to see which one has the weapons?". Or screw that, why not just pick up the boxes and start using them as weapons? This match was just a level of stupid I wasn't prepared for. Boy was it bad.
Knockouts Lockbox Challenge (TNA 2010) = OK, now I'm just picking on them, but they deserve it for ideas like this. Basically, the four girls who got pinfalls earlier in the night would get to pick a box. One of the boxes contained the KO Title. That's right, you could win a championship just by opening a box. And this wasn't a vacated title or anything. Other prizes also included Victoria's (Tara to TNA fans) pet spider and the right to strip in front of the live audience. OK then.
Reverse Battle Royal (TNA 2006-2007) = I don't passionately hate this one as much as other people do because once you get passed the first portion, it isn't that bad. I just don't understand why guys would have to fight to get in the ring, and they make the act of getting over the top rope and into the ring look unrealistically difficult just for the sake of this match. it is dumb.
Various Lockdown Gimmick Matches (Lockdown 2005-2015) = I already touched up on this with the Electrified Cage, but there are many other examples of TNA's ridiculous attempts to differentiate all 7-9 cage matches on a 3 hour PPV. The simple act of having that many cage matches is stupid enough on its own, but some of the lame gimmicks they attached to those cage matches were even sillier. Like how about a 2 out of 3 Falls Match with the 3rd fall being a blindfold match? How about a match where we lock 12 men in the cage and they get eliminated by getting handcuffed to the cage. Or how about an arm wrestling match inside of a cage? Or how about a straight up blindfold match inside of a cage? Or how about Steel Cage street fights...which completely negates the whole reason for having a cage?
Feast or Fired (TNA 2007-present) = OK, I promise this is the last TNA one. I hate this match so much. Not only is a lame knockoff of Money in the Bank, but the idea that anybody would willingly gamble their jobs and play Russian Roulette with their career makes no sense to me. It is also one of the only matches I can think of where winning can result in a punishment. Yeeeeeeah.