Mad Man Pondo
Upon the title's creation, CZW recognized Derek Domino as the first CZW Iron Man Champion on February 13, 1999 at their Opening Night event. Domino immediately had to defend the title that night against Lobo, who went on to win the match and the championship. On June 10, 2000 at CZW's Caged To The End event, Mad Man Pondo defeated Wifebeater to win the championship. However, on July 22, 2000 at CZW's No Rules, No Limits event, Wifebeater was awarded the championship without facing Pondo in a match for unknown reasons. Instead, that night Wifebeater defended the title against Nick Gage, who went on to win the title. During Lobo's third reign CZW held their Breakaway Brawl show on June 9, 2001. A Triple Threat Deathmatch for the CZW Iron Man Championship occurred involving Nick Mondo, Wifebeater, and Mad Man Pondo, which Mondo won to become champion. Lobo was not involved due to a broken leg injury he sustained from the night before.