Punk began competing for the promotion Independent Wrestling Association Mid-South. He won the IWA Mid-South Light Heavyweight Championship 2 times and the IWA Mid-South Heavyweight Championship five time, defeating the likes of A.J. Styles, Colt Cabana and Eddie Guerrero. He feuded with wrestlers like Colt Cabana and Chris Hero. During his feud with Hero, they competed in a 55-minute TLC match, a 93-minute two out of three falls match, and many 60-minute time limit draws. During the feud with Cabana, Punk wrestled him in many different matches. The matches he had with Cabana would lead Punk to being hired by Ring of Honor. He chose not to compete for Mid-South anymore from February 2003 until May 2004 because he said that he was protesting the mistreatment of Chris Hero from Ian Rotten. Punk returned to the company and performed as both a wrestler and commentator. He stayed with the company until 2005 when he was signed by the World Wrestling Entertainment. His last match in the company was against Delirious which ended in a 60-minute time limit draw