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His last appearance in IWA: Mid-South was on July 2, 2005 in which he competed in a 60-minute time limit draw against Delirious.
Initially, Punk joined Ring of Honor (ROH) as a crowd favorite, but quickly became a villain in a feud with Raven that featured numerous variants of no disqualification matches.
During Punk's time in IWA: Mid-South, he had high profile feuds with Colt Cabana and Chris Hero while also rising to the top of the roster winning the IWA Mid-South Light Heavyweight Championship twice and the IWA Mid-South Heavyweight Championship on five separate occasions, beating stars like A. Styles, Cabana and even Eddie Guerrero for that Championship.
Punk's feud with Hero included a 55-minute TLC match,a 93-minute two out of three falls match, and several 60-minute time limit draws.
There, he was the first head trainer of the ROH wrestling school.
Also while competing in ROH, Punk won both the company's championships.
Punk's matches with Cabana led him to being hired by the Ring of Honor promotion.
From February 2003 until May 2004, Punk refused to wrestle for IWA: Mid-South, because he claims that this was in protest to Ian Rotten's mistreatment of Chris Hero in the company.
The scuffle reportedly stemmed from an ROH show in which Hart performed three unplanned spots putting several other wrestlers in danger of injury.Throughout his career, Punk has consistently used the gimmick of being an outspoken, sharp-tongued, and straight edge iconoclast.