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#3 (Tied) Undertaker, Randy Orton and Brock Lesnar - 5 world title matches at WWE Royal Rumble
In the 13 years between Royal Rumble events in 1991 and 2004, no superstar was involved in more World Title matches than The Undertaker.
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His maiden appearance was in the iconic 1992 Royal Rumble match, and this was followed by three more unsuccessful attempts at the WWF Title. He failed twice in the subsequent 5 years at the Royal Rumble, with losses to WWF Champions Yokozuna and Shawn Michaels in Casket matches, in 1994 and 1998 respectively.
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Sandwiched between the two Casket match losses is his disqualification victory over Bret Hart in 1996, thanks to and interference from Diesel. His only legitimate victory was his successful World Heavyweight Title defense against Rey Mysterio in 2010.
Given their long history inside the ring, it feels perfect to have Brock Lesnar's name listed along with Taker. Brock's first WWE Title defense came during his first stint with the company, at the 2004 Royal Rumble, against Hardcore Holly.
His more notable matches, however, have been his acclaimed WWE Title defense against John Cena and Seth Rollins in 2015, and his incredible Universal Title defense against Finn Balor in 2019. He successfully defended the Universal Championship a year before that as well, in a gargantuan match against Braun Strowman and Kane. His only unsuccessful attempt at the World Title was at the 2016 Royal Rumble, where he was dispatched by the Wyatt Family from the Royal Rumble match.
Completing this trifecta is the only superstar who has an actual shot of being in a World Title match this year as well - Randy Orton. Orton's first appearance came way back in 2005, where he lost to World Heavyweight Champion Triple H. Since then, he has defended the WWE Title against Jeff Hardy in 2008 and lost to Sheamus and The Miz in 2010 and 2011 respectively. His last World Title match was his successful defense of the WWE World Heavyweight Title against John Cena in 2014.
