|Year Presented||CWMC Number||Courtesan of the Year||Brothel of the Year||Small Brothel of the Year||Other|
|1998||CWMC 2 a||Katherine Leigh - Sagebrush||Sagebrush Ranch||None awarded||GP's Choice - Bashful|
|1999||CWMC 3||Cindy Spice - Sagebrush||Sagebrush Ranch||None awarded|
|2000||CWMC 4 a||Nikita - Kitty's||Kitty's Cathouse (now The Love Ranch)||None awarded||John of the Year - Flyfisher|
|2001||CWMC 5 a||Nikita, Adele, Shannon b||Sagebrush Ranch||None awarded||GP's Choice - Alexa Albert|
|2002||CWMC 6 c||Summer - Chicken Ranch||Chicken Ranch||Shady Lady Ranch||Most Improved Brothel - Sheri's Ranch|
|2003||CWMC 7 d||Chay - Sheri's Ranch||None awarded||None awarded|
|2004||CWMC 8||Shanice, Chay e||Wild Horse Adult Resort and Spa||Shady Lady Ranch|
|2005||CWMC 9||Tabitha - OBR, World Famous||Wild Horse Adult Resort and Spa||Shady Lady Ranch|
|2006||CWMC 10||Carolina - Wild Horse||Wild Horse Adult Resort and Spa||Shady Lady Ranch|
|2007||CWMC 11||Jenny Lane - Moonlite Bunnyranch||Wild Horse Adult Resort and Spa||Shady Lady Ranch|
|2008||CWMC 12||Anna Suvari - Moonlite Bunnyranch||Wild Horse Adult Resort and Spa||Shady Lady Ranch|
|2009||CWMC 13||Anna Suvari - Moonlite Bunnyranch||Moonlite Bunnyranch||Shady Lady Ranch|
|2010||CWMC 14||Anna Suvari -Moonlite Bunnyranch||Moonlite Bunnyranch||Shady Lady Ranch|
|2011||CWMC 15||Lexy - Chicken Ranch||Love Ranch - Moundhouse||Inez's D&D|
|2012||CWMC 16||Envy - Sheri's Ranch||Sheri's Ranch||Dovetail Ranch|
|2013||CWMC 17||Destini - Sheri's Ranch||Sheri's Ranch||Alien Cathouse|
|2014||CWMC 18||Carerra - Mustang Ranch||Mustang Ranch||Dovetail Ranch|
a These awards were sponsored by GP of the GPPAYS.com
b Three Courtesan of the Year awards were presented this year because of a 3-way tie in the voting. Nikita worked at Kitty's while Adele and Shannon worked at Sagebrush.
c These awards were sponsored by Arctic Bear.
d No public voting was held this year and the award was sponsored by Curious.
e Two Courtesan of the Year awards were presented this year because of a tie in voting. Shanice worked at the Wild Horse while Chay worked at the Shady Lady.
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