10 WORST Matches From WWE’s Biggest Gimmick Bouts

1. Hell In A Cell

The Match: The Undertaker vs. Big Boss Man at WrestleMania XV.

Why It Was The Worst: If you've ever watched even a few minutes from this painful match, then you'll know exactly why this one tops the list as the worst WWE gimmick bout of all time. Yep, it's not just the worst Hell In A Cell match, but arguably the worst ever generally. The Undertaker vs. Big Boss Man at 'Mania XV was just that bad.

The finish tried to be shocking for the sake of it too.

Nothing went right. Boss Man's handcuffs broke (what kind of law man has cuffs that break?), the crowd weren't into it once they realised that neither man was going to take a Foley bump and the image of Boss Man being hanged was 'Attitude' era excess personified.

People complain about what HIAC has become nowadays, but not even WWE's worst attempt today could top this.

What do you think are the worst matches from these stipulations? For more like this, check out 10 WWE PPVs That Aren’t As Good As You Remember and 22 Craziest Moments From WWE Extreme Rules 2020!