Wifebeater debuted in
Combat Zone Wrestling on August 21, 1999, at "Pyramid of Hell" on the losing end of a match against
Trent Acid. On September 18, 1999, Wifebeater defeated
Nick Gage to win his first
World Heavyweight Championship. Wifebeater held the title until November 20, 1999, when he lost it to
John Zandig. Wifebeater went on to win the CZW Heavyweight Championship two more times and the
Iron Man Championship four times. He also teamed up with
Justice Pain to form the
H8 Club and win the
World Tag Team Championship. Wifebeater and Justice Pain lost the titles to Nick Gage and Nate Hatred, who later also referred to themselves as the H8 Club. After their title loss and failure to regain the titles in a rematch, Wifebeater and Justice Pain broke up and began feuding. This feud ended at
Cage of Death III inside the Cage of Death for the CZW World Heavyweight Championship where Pain defeated Wifebeater. During one period in 2001, Wifebeater was a member of the stable "Big Dealz" along with
John Zandig,
Nick Mondo,
Jun Kasai, Z-Barr, and
Trent Acid. In 2002, Wifebeater won the first-ever CZW Tournament of Death after defeating
Nick Mondo in the finals. He wrestled a
retirement match in November 2002, but made a return a year later in the same month to join Zandig's team for
Cage of Death V. In 2004, he won the
third Tournament of Death after defeating
Necro Butcher in the finals. Later in the year, Justice Pain returned and rejoined Wifebeater to reform the H8 Club. They targeted the H8 Club of Gage and Hatred and defeated the pair at
Cage Of Death 6 on December 11, though after their victory Justice Pain turned on Wifebeater. Prince subsequently made infrequent appearances in CZW, including a run in on the ROH wrestlers during a big brawl between CZW and ROH at ROH's "Arena Warfare" in early 2006. His final match to date was at CZW's event
Trapped on August 12, 2006, filling in for a vacant
J.C. Bailey, where Wifebeater defeated Danny Havoc in a barbed wire cage. ==Championships and accomplishments==