10 Wrestlers Reveal The Worst Matches Of Their Career

5. Jake Roberts

Roberts' first major appearance for WCW was at Clash of the Champions, where his team won an elimination tag match with him getting the pin over Sting, building to a feud between the pair. This led to Jake’s single WCW pay-per-view match against Sting at Halloween Havoc in 1992. Their match was determined via Spin the Wheel: Make the Deal, a Wheel of Fortune-like gimmick. There was a host of gimmick matches on the wheel, but because the wheel itself was not rigged, Roberts nor Sting for real knew what kind of match they’d be wrestling in until the wheel stopped.

Of course it stopped on the worst option possible - the Coal Miner's Glove match. The rules of the match are a leather glove hangs atop one of the ring posts about 10 feet high and the first participant to gain possession of the glove gets to use it on his opponent. It’s as bad as it sounds. Sting pinned Jake after hitting him with the coal miner's glove, with Jake’s snake turning on him afterwards.

Jake’s said of the match:

"Great thing the commercials were good because that was it. The match stunk and so did the idea. That was such a horrible thing to choose. What in the hell, man. I'm not climbing no pole, are you serious Bill (Watts)? That is the best thing that you could come up with? I thought it was ridiculous and the match was one of my worst matches. Sting wasn't very excited to wrestle back then and he had gotten tired of being the guy that everybody depended on to bring in the big house and he was getting lazy because he had that contract and that is the bad thing about contracts is that guys get lazy and are like well, I'll get all my money anyway.”

It’s saying something if Jake regards this as the worst match he’s ever been a part of, given his blindfold match at WrestleMania VII against ‘The Model’ Rick Martel where neither of them could see or the Heroes of Wrestling catastrophe he competed in.