Most Challenge Cups by a Player

6 Cup Wins:

Hugh Jazz - (S51,S53,S56,S58,S61,S63)
Aaron Wilson - (S51,S53,S56,S58,S61,S63)

5 Cup Wins:

Reggie Williams - (S8, S9, S12, S15, S16)
Bubba Nuck - (S24, S26, S29, S32, S38)
Esa Anrikkanen - (S27, S29, S32, S40, S42)
Michael Boychuk - (S27, S29, S32, S40, S42)
Alex Mack - (S27, S29, S32, S40, S42)
Nicholas Pedersen - (S27, S29, S32, S40, S42)
Randy Randleman - (S27, S29, S32, S40, S42)
Joe Kurczewski - (S32, S40, S42, S45, S54)
Samuel Michaud - (S51,S53,S56,S58,S61)
Michael Scarn - (S55,S56,S58,S61,S63)

4 Cup Wins:

Pavol Skvoznak - (S1, S4, S6, S12)
Laraque Obama - (S8, S13, S15, S16)
Alexander Andrezjeck - (S13, S15, S16, S17)
Vinny Chezno - (S13, S15, S16, S17)
Mikhail Krivokrasov - (S15, S16, S20, S21)
Brendan Gibbon - (S14, S20, S21, S28)
Jakob Tanner - (S24, S26, S30, S31)
Benjamin Reid - (S23, S30, S31, S33)
Nathan Russell - (S23, S30, S31, S33)
Blake Sherrill - (S23, S30, S31, S33)
Bennett Jones - (S30, S31, S33, S38)
Richard C. Hocolate - (S29, S32, S40, S42)
Crossfit Jesus - (S34. S38,S44,S47)
Sven Brokstad - (S41,S43,S47,S49)
Skao Anazibf - (S51,S53,S56,S58)
Hippo Passamus - (S46,S48,S55,S60)
Alexander Selich - (S46,S48,S55,S60)
Mitchell van der Heijden - (S54,S58,S61,S63)
Rikard Hammarberg - (S56,S58,S61,S63)
A Jobin - (S56,S58,S61,S63)
Theo Morgan - (S56,S58,S61,S63)
Guy O'Shea - (S56,S58,S61,S63)
Rotticus Scott - (S56,S58,S61,S63)

3 Cup Wins:

Sergei Karpotsov - (S1,S3,S4)
Castiel Lee - (S1,S3,S4)
Jay McDonald - (S1,S3,S4)
Alexander Cattermole - (S2,S3,S4)
Dorian Greiser - (S2,S3,S4)
Eric Scheib - (S3,S8,S9)
Ron Bolt - (S6,S8,S9)
Gene Parmesan - (S10,S15,S16)
Michael Haan - (S13,S15,S16)
Cole Reinhart - (S13,S15,S16)
Lucas Smith - (S13,S15,S16)
Ja'Far Dar - (S10,S12,S18)
Daniel Passarella - (S10,S12,S18)
Jonas Gustavo - (S14,S20,S21)
Chris Partlow - (S14,S20,S21)
Shawn Velevra - (S17,S20,S21)
Maxim Horvat - (S19,S20,S21)
Willie Weber - (S15,S16,S23)
Riko Muerto - (S15,S16,S24)
Gustav Grimm - (S18,S24,S26)
Claude Perron - (S18,S24,S26)
Simeon Mars III - (S19,S24,S26)
Jakub Aittokallio - (S15,S16,S28)
Chico Salmon - (S20,S21,S28)
Charlie Winchester - (S23,S30,S31)
Rider Clitsome - (S24,S26,S31)
Yorgen Bartenberry - (S27,S29,S32)
Jaime Hill - (S27,S29,S32)
Kriss Labsvards - (S27,S29,S32)
Schnitinfritz Jagr - (S27,S29,S32)
Fernando Pergher - (S27,S29,S32)
Hunter Wong - (S27,S29,S32)
Sachimo Zoidberg - (S27,S29,S32)
Tim Buckner - (S30,S31,S33)
Patrikov Bure - (S30,S31,S33)
Jasper Clayton - (S30,S31,S33)
Mia Landvik - (S30,S31,S33)
Mikke Laukkanen - (S30,S31,S33)
Mainio Makinen - (S30,S31,S33)
Roman Morenov - (S30,S31,S33)
Raven Silverwing - (S30,S31,S33)
Mikael Talo - (S30,S31,S33)
Tommy Creller - (S22,S32,S34)
Liam Kinsler - (S20,S21,S36)
VLAD McZehrl - (S27,S34,S37)
Winston Windsor - (S28,S36,S38)
Jonathan Lundberg - (S30,S31,S39)
Hunky Monkey - (S32,S38,S40)
Adam Kaiser - (S36,S40,S42)
Leafer Rielly - (S41,S43,S46)
Dani Forsberg - (S40,S43,S47)
Beaujeaux Biscuit - (S41,S43,S47)
Ted Glass - (S41,S43,S47)
Karsten Kadinger - (S41,S43,S47)
Alex Light - (S41,S43,S47)
Ludwig Koch Schroder - (S41,S43,S47)
Trevor Wilson - (S41,S43,S47)
Gabriel Wong - (S41,S43,S47)
Willy Mack - (S37,S45,S49)
TJ Bayley - (S46,S48,S49)
Casey Creller - (S40,S42,S50)
Ostap Maksimov - (S40,S42,S50)
Mike Izzy - (S40,S42,S50)
Louie Garrett - (S40,S48,S51)
Cassius Darrow - (S46,S46,S55)
Viktor Marius - (S46,S48,S55)
Jax Duggan - (S51,S53,S56)
Gabriel Johnson - (S51,S53,S56)
Dale Miller - (S51,S53,S56)
Robert Phelps - (S51,S53,S56)
Monkey D. Luffy - (S46,S55,S60)
Devin Basher - (S58,S61,S63)

Updated for S63 Season

Note: This is cups per Player, not User.