Wiles' first known match in Extreme Championship Wrestling (ECW) was against Axl Rotten in a house show in Waltham, Massachusetts, in a losing effort. He wrestled Sabu, Louie Spicolli and Balls Mahoney, but failed to defeat them. Wiles challenged Taz for the ECW World Television Championship in a singles match in the same venue in Waltham, Massachusetts to a losing effort.
Wiles would work alongside Lou E. Dangerously's Dangerous Alliance, teaming up with C.W. Anderson, proceeding to feud against Roadkill and Danny Doring and The Hardcore Chair Swingin' Freaks (Balls Mahoney and Axl Rotten). The brink of the feud with Roadkill and Doring happened at ECW Living Dangerously. Doring and Roadkill's manager Elektra turned on them, allowing Anderson and Wiles to pick up the win. Wiles soon left the Dangerous Alliance sometime after Cyberslam 2000 as a singles competitor, facing Nova, Michael Shane and Steve Corino in several matches on ECW Hardcore TV and ECW on TNN tapings. He formed a tag team with "The Prodigy" Tom Marquez dubbed as the Sideshow Freaks. They fought Doring and Roadkill, and Christian York and Joey Matthews. The team would eventually split up.
Wiles wrestled at the final Extreme Championship Wrestling pay-per-view event Guilty as Charged, scoring the victory against Mike Bell in a dark match.