Big Show & The Undertaker vs. Kane & X-Pac- SummerSlam 1999
This was somewhat of a typical tag team match from the Attitude Era. At times this match seemed a little bit clustered with everyone fighting in the ring at once, but overall it was a solid match. It’s a fairly fast-paced, physical match with The Undertaker and Big Show picking up the victory and winning the Tag Team Titles (I believe it was Big Show’s first Title win with WWF/E).
The Undertaker vs. Mankind- SummerSlam 1996
Oh, the very odd match types of the 90s! This was the first of the short-lived Boiler Room Brawl matches, so it’s obviously not one of the most technically sound wrestling matches you’ll ever see. This match is more of a “what can I beat the other guy up with?” kind of match. That doesn’t mean it was a bad match though! It’s still a very entertaining, brutal match. It’s probably in the Top 10 matches of 1996. This match is also noted as when Paul Bearer turned on The Undertaker and aligned himself with Mankind.
The Undertaker vs. Bret Hart- SummerSlam 1997
This was an early Attitude Era match that helped set up the infamous Michaels/Hart match at Survivor Series later that year. The Undertaker was the current champion, and Shawn Michaels was put as referee in the match to make sure Bret didn’t leave as champion. Of course, things don’t always go as planned with special referees!
The Undertaker vs. Stone Cold Steve Austin- SummerSlam 1998
This match seems to be sort of forgotten when talking about WWF Championship matches in the 90s. It was a pretty solid main event with a clean ending (which was pretty rare in 98). It helped build up Stone Cold giving him a title defense and the sign of respect by The Undertaker at the end of the match. The highlight of the match for me was definitely the top rope double leg drop through the announce table done by The Undertaker. It was a great show of agility done by the Dead Man.
The Undertaker vs. Edge- SummerSlam 2008
This one seemed kind of obvious. How can you not have an amazing match when you have Edge vs. The Undertaker in Hell in a Cell? This was the last match of their amazing 2008 rivalry (arguably the best rivalry of the year), and it did not disappoint. Edge speared The Undertaker through the cell wall, The Undertaker chokeslamed Edge through 2 tables, Edge gets put through the canvas after the match, and the whole thing wasn’t even for a title! Fun fact: this is currently The Undertaker’s last SummerSlam match. If all works out well, we’ll get to see him square off against Lesnar at this year’s SummerSlam!
