90s
2000s
2010s
2020s
WILDCARD
100

These three superstars are tied for the most Royal Rumble wins from 1990-1999

Hogan, HBK, Stone Cold

100

Name the two general managers for the inaugural draft in 2002

Vince McMahon and Ric Flair

100

I was in the corner of a commentator for his match at WM27

Jack Swagger

100

We Are................

DIY

100

Say the next line of this song:

Rolling ever faster to this nightmare you have sewn

You had it all right in your grasp

200

I missed my cue at Wrestlemania 8, causing something that had never happened before...

Papa Shangooooo

200

Who won the Battle Royal at WM 17

Iron Shiek

200

I lost two matches at Wrestlemania in the 2010's

Undertaker

200

Name the only people to pin Cody Rhodes since his return 

Brock, Drew, Rock 

200

I was the 4th TNT Champion

Darby Allin

300

We fought the Bushwhackers at Wrestlemania 10

Heavenly Bodies

300

This wrestler won both World titles, IC, European, Tag, and KOTR- all in the 2000's

Kurt Angle 

300

We were the second match of WM 33

Jericho and Owens
300

After 8 years, I made my return at WM 40 (Hint: I was not involved in the main event)

Bubba Ray Dudley

300

We beat Angelico and Jack Evans at DON 2019

Best Friends

400

We won the Tag Titles in 1991 and 1997

Legion of Doom

400

This wrestler won his first WWE World Title in 9 years

Hulk Hogan

400

This man beat Tyson Kidd by DQ in his NXT debut match in 2014

Finn Balor

400

I am the only active wrestler that fought in WCW

AJ Styles

400

I was number 16 in the 1992 Royal Rumble

Jake Roberts

500

This was the first ever match at In Your House 1

Bret Hart vs. Hakushi

500

What month and year did WWF change its name to WWE

May 2002

500

Name the main event of Battleground 2014

Cena vs. Kane vs. Orton vs. Reigns 

500

I wrestled for WWF, then TNA, then came back to WWE, and I won my match at WM40

R Truth

500

I almost left WWF in 1992, and I was so close to leaving that I had to drop my title. 

Bret Hart