The legendary rivalry between The Undertaker and Brock Lesnar had a few different chapters. WWE used Undertaker's prestige to help Lesnar get to a new level on multiple occasions. Everyone will remember Brock beating Undertaker inside of the Hell in a Cell structure as a rookie or ending the undefeated WrestleMania steak, but quite a few things remain under the radar as years go by.

The duo definitely had chemistry to work matches against each other throughout different chapters of their careers. Undertaker and Brock had enough matches, moments and segments to have overlooked tidbits of their time together. Find out more about what made their rivalry work beyond the obvious memories from their history in WWE.

8 Paul Heyman Busted Open During First Hell In A Cell Match

Paul Heyman Brock Lesnar

One overlooked memory of The Undertaker vs Brock Lesnar feud featured a rare moment of Lesnar's manager Paul Heyman getting physical. Heyman took bumps when needed for big stories, but he usually would not get involved in the physical nature of taking moves.

Undertaker grabbing Heyman's tie from inside of the Hell in a Cell structure saw him yanking on it to hit Heyman multiple times. The story was that no one could escape the violence as Heyman shockingly bled during the match eventually won by Brock.

7 The Undertaker Set Up UFC Confrontation Was A Work

Undertaker Brock Lesnar UFC

The time away from WWE for Brock Lesnar saw his star power only growing when finding success in UFC. There was a strange real moment between The Undertaker and Brock where Lesnar was walking to the back after his fight and had an awkward interaction with his former foe.

Undertaker saying the words "you wanna do it?" became a top trending topic the next day. Interviews in later years saw Undertaker admitting he was there to try to stir up trouble with Brock and attempt to sell a future match if he did return to WWE, which happened.

6 Brock Threatening The Undertaker's Wife

Brock Lesnar Undertaker's Wife

The first chapter of the feud between Brock Lesnar and The Undertaker is often forgotten, but they had so many intense moments. Undertaker's wife Sara was pregnant at the time and took part in a backstage segment with Lesnar.

The terrifying moment saw Brock cornering Sara and putting his hand on her stomach before threatening the entire family. Undertaker's character needed something like this to make it even more personal heading into their big PPV matches.

5 One Of Two Singles Programs To Have 2 Hell In A Cell Matches

The Undertaker Vs Brock Lesnar Hell In A Cell

WWE tries to keep their talents away from having the same match with the same stipulation multiple times. The Undertaker and Brock Lesnar are one of just two singles matches to have multiple bouts inside of the Hell in a Cell structure.

Their first match featured Brock winning to cement his status as the dominant rookie WWE Champion. Lesnar won the match in the structure again about thirteen years later when they faced off for the final time. John Cena vs Randy Orton is the other rivalry to have multiple matches inside of the Hell in a Cell.

4 Brock Went To Hospital With The Undertaker After WrestleMania XXX

Brock Lesnar The Undertaker WrestleMania 30

The standoff personality of Brock Lesnar sees him known for rarely wanting to be around others. Lesnar is known for clocking in and out of the job, but he did go out of his way to check on The Undertaker after he suffered a scary injury.

The infamous WrestleMania XXX match between Brock and Undertaker saw the undefeated streak finally end. However, Undertaker suffered a concussion during the match and collapsed backstage. Lesnar and Vince McMahon went to the hospital following the ambulance to make sure Undertaker was progressing positively for his health.

3 The Undertaker's Respect Turned Brock Face

Brock Lesnar Hell In A Cell

Brock Lesnar had the most dominant first year in WWE history. The win over The Rock to become WWE Champion was enough to make him a main eventer, but the next program with The Undertaker added even more momentum.

Undertaker putting over Brock clean in the Hell in a Cell match led to the fans showing more love to Lesnar. WWE decided to move forward with turning Brock face by having Undertaker show him respect afterwards. The legend of Undertaker has seen his respect helping other stars like Jeff Hardy and John Cena earlier in their careers, and WWE decided to go even further with that for Lesnar.

2 Title Match Set Up The Undertaker Feud Vs Vince McMahon

The Undertaker Vs Vince McMahon

The Undertaker entered another feud with Brock Lesnar during the latter's first WWE stint once again as a heel. Vince McMahon was associating with Brock as heels, and he got involved in the No Mercy 2003 Biker Chain match between Undertaker and Lesnar.

The WWE Championship match ended with Vince pushing Undertaker off the top rope and allowing Brock to hit him with the biker chain for the win. WWE booked this finish to set up the Buried Alive match between McMahon and Undertaker one month later.

1 Brock Didn't Want To Work With "Deadman" Gimmick In 2004

The Undertaker WrestleMania 20

WWE was shocked when Brock Lesnar decided to leave after WrestleMania XX. The contract expiring gave Brock the option to leave the business and chase his dream of trying to play football. One forgotten factor featured the Wrestling Observer sharing WWE's plans for Lesnar after that show before they knew his fate.

The hope was for Undertaker to work his returning Deadman character against Brock over the next few months to gain some huge wins. Lesnar was unhappy about this and felt that gimmick made Undertaker's opponents look bad since he often didn't sell. The small factor was one of many reasons for Brock leaving, but he did end up working with the Deadman version of Undertaker a decade later.