#1 Curt Hawkins
Well, of course. Curt Hawkins had to appear somewhere on this list – he’s the biggest serial loser in WWE history, after all. As of the time of writing, he has lost an unprecedented 269 matches in a row, including five on Raw in the last 12 months.
In terms of television time, the former Edgehead has appeared more frequently in recent weeks than at any time since he returned to WWE in 2016, but his reunion with Zack Ryder is yet to result in a victory for the former Tag Team champions.
Hawkins’ last victory came on SmackDown Live against Apollo Crews in November 2016. However, if we’re looking solely at his record on Raw, the stats show that he has never won a match on the red brand, which is astonishing when you consider that he debuted in WWE in 2007 and competed in his first Raw match in 2011.