#1 Brock Lesnar is undefeated against Randy Orton (7-0)
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Brock Lesnar and Randy Orton came up to the main roster at around the same time, in the spring of 2002. Both competitors were polishing their skills down in OVW in the early 2000s. It has been around two decades since both Brock Lesnar and Orton made their way to WWE, and the latter is yet to score a win over The Beast Incarnate in a singles match. Before they made their way to the main roster, Brock Lesnar had scored four straight wins over Orton in singles competition.
The two met again on an episode of SmackDown in September 2002. Brock scored a victory again, and it would be 14 years before they met again in the ring. In what was dubbed a dream match by many, Brock Lesnar and Orton faced off at SummerSlam 2016. The match became infamous for Lesnar's brutal beatdown on Orton, which left him lying in a pool of his own blood.
A month later, the duo met again at a live event, this time in a "Suplex City Death Match". Lesnar was victorious again. The two WWE legends never crossed paths after this match.