Ranking all 25 WrestleMania matches of The Undertaker

20. The Undertaker vs. Sycho Sid – WrestleMania 13

The WWE Championship picture surrounding WrestleMania 13 became a little chaotic after Shawn Michaels vacated the title during his infamous “I lost my smile” promo. The Undertaker was placed in a Fatal 4-Way match at In Your House 13 with Bret Hart, Stone Cold Steve Austin and Sycho Sid, a match that Bret Hart won. However, he lost the title to Sid just a day later on Monday Night RAW and since ‘Taker had been the runner-up in the Final Four match, he was put into the main event of WrestleMania 13, which really is a good thing seeing as how we got the Austin vs. Hart match out of it. Unfortunately, the match between the two big men didn’t live up to its main event status.

The first 15 minutes of the match were painful to watch and that still rings true today. Sid never had the pedigree for the main event (WrestleMania VIII, anyone?) and it showed in full force that night in Chicago. There were so many rest holds like a bearhug, a Camel Clutch and a chinlock that just killed the live crowd (and that’s tough to do in the Windy City). And while The Undertaker tried a few different times to make things interesting, he couldn’t do it on his own.

The crowd came back a little at the end when The Undertaker hit a nice leaping clothesline from the top rope and did the throat-slashing gesture that became so popular as the years went on. The Undertaker attempted a Tombstone but Sid countered it into one of his own (probably his best move of the night) and went for an Undertaker-style pin but The Deadman kicked out at two. The action spilled to the floor and then Bret Hart got involved and hit Sid with a couple of chair shots, which was legal as there was a no DQ stipulation for this one. ‘Taker hit a chokeslam for a two count back on the inside but Sid soon had control again and went for a powerbomb but Bret Hart came back out and interfered yet again. Sid went after him on the apron but Bret choked him with the top rope and sent him back flying right into a Tombstone and The Undertaker had his second world title. 6-0.