[2] The following month, he competed in the second annual CZW Tournament of Death where he lost to Nick Mondo in a deathmatch involving light tubes.

[8] He also competed in the fifth annual IWA Mid-South King of the Deathmatch tournament in August, where he defeated 2 Tuff Tony, Necro Butcher, and Ian Rotten, before losing to Mad Man Pondo in the final.

[9][10] On November 21, Bailey won a three-way match against Dutt and Nate Webb to win the IWA Mid-South Light Heavyweight Championship for the third time.

[17] The following month, on August 13, Bailey defeated Necro Butcher in a No Ropes Barbed Wire Death Match to win the Ultraviolent Underground Championship for the second time.

[23] On September 16, 2006, he competed in the first Masters of Pain tournament where he lost to the "Crazy Monkey" Jun Kasai after defeating 2 Tuff Tony and Corporal Robinson.

In December 2009, Bailey returned to CZW at Cage of Death 11, attacking Thumbtack Jack who had just won a no-ropes barbwire match against Nick Gage.

Bailey and Gram were soon joined by tHURTeen, the returning Brain Damage and Masada in The Cult Fiction, and began a feud against fan favorites Danny Havoc, Drake Younger, Scotty Vortekz and Eddie Kingston who were dubbed The Suicide Kings.

After pictures of Bailey's mugshot showing him covered in blood were released to the public, a local activist group held a vigil and filed a complaint to the town of Bardstown.