Players with exactly five wins since the start of Season 20 (listed under the season in which their regular-play loss took place):Season 20
Chris Miller - 2004 semifinalist; UToC semifinalistSeason 21
Kerry Breitenbach - 2006 quarterfinalistSeason 22
Maria Wenglinsky - 2006 semifinalist; BotD first round
Bob Mesko - 2006 semifinalist
Craig Westphal - 2007 semifinalist
Celeste DiNucci - 2007 champion; BotD first roundSeason 23
Jeff Spoeri - 2007 semifinalist
Steve Unite - 2007 quarterfinalist
Andrew Rostan - 2007 quarterfinalist
Mehurn Etebari - 2007 quarterfinalist
Cathy Lanctot - 2007 quarterfinalistSeason 24
Paul Glaser - 2007 semifinalist
Lisa Klink - 2009 quarterfinalist
Cora Peck - 2009 semifinalist
Aaron Schroeder - 2009 third place
Mark Wales - 2009 semifinalistSeason 25
Matt Kohlstedt - 2009 semifinalist
Liz Murphy - 2010 semifinalistSeason 26
Stefan Goodreau - 2010 third place
Terry Linwood - 2010 semifinalist
Dave Belote - 2010 semifinalist
Paul Kursky - 2011 quarterfinalistSeason 27
Kara Spak - 2011 semifinalist
Tom Kunzen - 2011 quarterfinalist
Jay Rhee - 2011 semifinalistSeason 28
David Menchaca - 2013 quarterfinalistSeason 29
Paul Nelson - 2013 semifinalist
Kristin Morgan - 2013 third place
Joshua Brakhage - 2014 semifinalist
Rebecca Rider - 2014 semifinalistSeason 30
Rani Peffer - 2014 quarterfinalist
Jerry Slowik - Not invited
Sarah McNitt - 2014 quarterfinalistSeason 31
Vaughn Winchell - ???
John Schultz - ???
Kristin Sausville - 2015 quarterfinalist
Andrew Haringer - ???
Dan Feitel - ???
Brennan Bushee - ???
Scott Lord - 2015 quarterfinalist
I'll also throw in a link to this table
that shows how players performed in the ToC based on where they finished on that tournament's leaderboard (their "seed," if you will, or the type of tournament in which they earned their automatic bid). In addition to the 2014 ToC being the first with three super-champs in the final, it was also the first in which the top three seeds reached the final.