The Undertaker's legendary career is coming up on its 30th anniversary. That day officially arrives at the 2020 installment of the Survivor Series. It was indeed at that very event in 1990 that The Deadman made his debut and began arguably the greatest run any wrestler has ever had.
It wasn't just his debut, either. The Undertaker has had many iconic moments in Survivor Series history including his first WWE Title win, a classic return in 2005, and the end of his American Badass gimmick. He's had some of his greatest matches at the event and unfortunately, a handful of his absolute worst.
10 Worst: The Undertaker vs. Vince McMahon - 2003
When The Undertaker debuted in 1990, he probably never imagined he would've wrestled against his boss at the event 13 years later. This wasn't an ordinary match, either. It was held under Buried Alive rules.
Vince was always a standout entertainer but he's not a wrestler. His matches were very hit or miss and unfortunately, this one mostly missed the mark. It was a lot of lackluster brawling until Kane interfered to help Vince bury his brother. The Undertaker wouldn't be seen again until WrestleMania XX, returning as The Deadman.
9 Best: The Undertaker vs. Big Show vs. Chris Jericho - 2009
Survivor Series 2009 saw two monumental triple threat matches for the top two championships. For the WWE Title, John Cena defended against Shawn Michaels and Triple H. World Heavyweight Champion The Undertaker also defended against a tag team.
In fact, he battled the Tag Team Champions, Jeri-Show. This brought together one of Undertaker's oldest rivals in Big Show and someone he rarely shared the ring with, Chris Jericho. The match proved to be a very enjoyable one that saw The Undertaker remain on top.
8 Worst: The Undertaker vs. Hulk Hogan - 1991
In terms of being an important and historic match, this should be on the "best" side of the list. A year after making his debut, The Undertaker headlined Survivor Series against Hulk Hogan. He was undefeated and fans assumed Hogan would send back the challenge of another monster.
So, it came as a true surprise when The Undertaker delivered a Tombstone onto a chair (with assistance from Ric Flair) to win the title. He wouldn't get to keep it long due to controversy in this match and the This Tuesday in Texas rematch, though. While an important bout, it wasn't very good.
7 Best: The Dream Team vs. The Million Dollar Team - 1990
The Undertaker's career started off with a bang. He was brought in as a surprise for The Million Dollar Team by Ted DiBiase. They partnered up with The Honky Tonk Man and Greg Valentine.
On the opposite side stood Dusty Rhodes, Koko B. Ware, and The Hart Foundation. The Undertaker was made to look like a true threat to everyone on the other team. It was a remarkable debut. He was only eliminated via countout and the entire match was a treat.
6 Worst: The Undertaker vs. Yokozuna - 1994
A coffin, two former WWE Champions, and Chuck Norris. That sounds like a recipe for success but it, unfortunately, wasn't for this main event. This stemmed from Royal Rumble 1994 when Yokozuna beat The Undertaker in a casket match with the help from about a dozen random heels.
After The Undertaker returned, he came for revenge. That meant another casket match against a Yokozuna who was scared of them, with Chuck Norris at ringside to prevent interference. Undertaker won a dull match and Norris barely did anything.
5 Best: The Undertaker vs. Batista - 2007
Nobody could've predicted that the best WWE rivalry of 2007 would be between Batista and The Undertaker. The two big men delivered classics at events like WrestleMania 23 and Backlash. However, things culminated inside Hell in a Cell at Survivor Series.
To be fair, they didn't exactly save their best for last but this was still a very good match. It saw the two put on a pretty brutal outing that had a huge twist at the end. Edge interfered disguised as a cameraman. He took out The Undertaker and placed Batista's arm over him, allowing The Animal to prevail.
4 Worst: The Undertaker vs. Kane - 1998
The history between Kane and The Undertaker is the stuff of legend. That was even the case back in 1998. At WrestleMania XIV and Unforgiven, they were opponents but by the time Breakdown came around, they worked together to stop Stone Cold. A month later, they met again at Judgement Day.
One more match was in the cards at Survivor Series as part of the Deadly Game tournament to crown a new WWE Champion. They had a boring bout with a surprisingly subdued crowd. With the help of Paul Bearer, The Undertaker won after hitting the Tombstone. He didn't make it past The Rock in the next round, though.
3 Best: The Undertaker vs. Mankind - 1996
It could be argued that Mankind was The Undertaker's greatest opponent. Mankind seemed to beat him at almost every turn when he first showed up in the company in 1996. That included wins at SummerSlam and in the first Buried Alive match.
Following the burial, The Undertaker returned at Survivor Series in Madison Square Garden. This was one of their best outings ever and saw Undertaker win by targeting Mankind's Mandible Claw hand. This return also sparked a great run for Undertaker that included a WWE Title reign in 1997.
2 Worst: The Undertaker vs. Kamala - 1992
After a classic debut and a WWE Title win in 1991, The Undertaker hit a relative low point at his third Survivor Series. He took on Kamala in a casket match. Similar to the angle they'd run with Yokozuna in 1994, Kamala was a character who was scared of the coffin.
The bout itself is actually quite bland. The Undertaker plodded around, did some punches and kicks, and Kamala wasn't very good at selling. That led to a match that is certainly not a bad one to skip.
1 Best: Team Alliance vs. Team WWF - 2001
Pretty much everyone agrees that the Invasion angle was a huge swing and a miss. WCW/ECW was booked to look supremely inferior and not many of their top stars showed up. That being said, the era actually led to some pretty tremendous matches featuring stellar talents. That was especially true when it all came to an end.
This "Winner Take All" bout saw Team WWF (The Undertaker, The Rock, Kane, Chris Jericho, & Big Show) take on Team Alliance (Steve Austin, Kurt Angle, Booker T, Rob Van Dam, & Shane McMahon). It was an outstanding match filled with great moments. Undertaker dominated at times but was eliminated after getting hit with a Stunner. Team WWF still came out on top.