5 WWE Superstars Paul Heyman has defeated

#3 and #2 Paul Heyman and Brock Lesnar defeat Jeff Hardy and Matt Hardy at WWE Judgment Day 2002 (May 19, 2002)

The Hardy Boyz

Brock Lesnar came up to WWE's main roster immediately after WrestleMania 18, and began wreaking havoc on both brands, with Paul Heyman managing Lesnar from the very beginning. The duo soon kicked off a feud with The Hardy Boyz. This led to a singles match between Brock Lesnar and Jeff Hardy at Backlash 2002, with Lesnar picking up the victory via TKO. The rivalry was far from over though, as The Hardy Boyz wanted to exact revenge on Lesnar and Paul Heyman.

Paul Heyman managed Lesnar from the very beginning

At Judgment Day 2002, Lesnar teamed up with Paul Heyman to take on Matt and Jeff Hardy, in Tag Team action. Initially, The Hardy Boyz gained control of the contest, but it didn't last long for the duo. As they tried to attack Paul Heyman, Lesnar threw Jeff Hardy on Matt Hardy, followed by which he delivered a thunderous F-5 on The Charismatic Enigma. This was enough for Paul Heyman to pin Jeff Hardy and pick up the victory for himself and Lesnar.