Osbourne ventured out onto the independent circuit in 1993. After brief stints in the NWA and ACW, he joined the Delaware-based East Coast Wrestling Association in the summer of that year. During this run he wrestled stars such as Tito Santana, Cheetah Master, Ace Darling, Blue Thunder, and The Bushwhackers. In 1996, Osbourne joined the Maryland-based Mid-Eastern Wrestling Federation (MEWF), and formed a tag-team with Rockin' Rebel known as Darkside. Together they dominated their division, winning the MEWF tag-team titles 5 times between 1996 and 1997. They also won the Virginia-based International Pro Wrestling Association tag team titles twice. During this time, Osbourne and Rebel were being scouted by the World Wrestling Federation. They worked for the company occasionally in dark matches and on house shows, both in singles and as a team, between 1994 and 2001. They also appeared regularly for the NWA.