10 Worst WWE Ladder Matches

6. Steve Austin vs. Vince McMahon & Shane McMahon - King of the Ring 1999

The 1999 King of the Ring pay-per-view was one of WWE’s worst ever, full of mostly short, bad matches and questionable booking decisions. 

The headline attraction wasn’t the King of the Ring tournament final or the WWE Title match between The Rock and The Undertaker, but a Handicap Ladder Match between Steve Austin and McMahons Vince and Shane, with full control of WWE on the line. 

Could it save what had been a washout of a show? Well, it was the most entertaining match of the night, but that doesn’t necessarily mean it was any good. 

Much of the match revolved around the ways in which Stone Cold could dish out punishment to his enemies, which was entertaining to a point, but the match featured too many flat spots and stuff that plain didn’t work. 

The McMahons took their lumps, yes, and it was enjoyable overall, but it’s not a good ladder match or anything. 

The finish was groan-inducing, too, as Austin looked to have the match won when some mysterious member of The Corporation fiddled with the wire holding the suspended briefcase, which ultimately allowed Shane to snatch it instead.