Ranking all 25 WrestleMania matches of The Undertaker

9. The Undertaker vs. Ric Flair – WrestleMania X8

On a night that will always be remembered for the “Icon vs. Icon” match that took place between Hulk Hogan and The Rock, WrestleMania X8 also featured a bout between two men who could also hold that title as The Undertaker took on Ric Flair.

The buildup to this match got extremely personal. Flair was the kayfabe co-owner of the company at the time and did not like The Undertaker attacking The Rock ahead of their match at No Way Out and ended up interfering in their match, causing The Undertaker to lose. This led The Undertaker to challenge Flair to a match at WrestleMania but The Nature Boy refused, saying he was no longer an active wrestler (always hilarious). So ‘Taker took it upon himself to attack Arn Anderson and Flair’s son, David, to goad him into it and it worked to perfection. The match was set for Toronto, and while it didn’t quite have the Rock-Hogan feel to it, it was still pretty solid.

This was a No Disqualification Match so you knew things were going to get bloody, especially with Flair involved, and they certainly did. They were both pretty aggressive from the get-go and while Flair got a few licks in, The Undertaker controlled things early and Flair was already bleeding after only a few minutes. Flair came back with a few chops (WOOOOOOO) but ‘Taker annihilated him in the corner with a clothesline and then gave him a superplex for good measure. Impressive spot for a big guy and an old guy. ‘Taker hit his leg drop on the apron and went for “Old School” but Flair knocked him off the top rope and eventually grabbed a lead pipe off of The Undertaker’s motorcycle at ringside and decked him with it, causing The Deadman to also shed some blood.

After a bit of back and forth, including ‘Taker taking a shot to the head with a road sign, Flair slapped on the Figure Four but The Phenom came back with a chokeslam for a two count, which he wasn’t happy about and pushed the ref back into the buckles. Eventually, Flair got up and sent ‘Taker into the ropes and Arn Anderson was in to hit a spinebuster. Cool spot. Flair got a near fall but ‘Taker was soon back up and beat down Arn, who also bled here, before finally finishing Flair off after about 19 minutes with the Tombstone. Another entertaining match. 10-0.