Osbourne got his start in the Philadelphia-based Tri-State Wrestling Alliance (TWA), run by radio personality Joel Goodhart, and became an early contributor to the city's hardcore wrestling style (Paul Heyman made his first ECW Television appearance by smashing his portable phone over Glen Osbourne's head).
Other notable TWA alumni include The Sandman, Rockin' Rebel, Jimmy Jannetty, Larry Winters, Tony Stetson, Johnny Hotbody, Max Thrasher, and D.C. Drake.
In September 1992, he defeated The Sandman in a match for the vacant Television Championship, becoming the youngest wrestler in history to hold the honor.
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.
Osbourne would also team with Derek Domino as The Natural Born Killers in the NWA and ECWA, and with Kevin Sullivan as The Dark Shadows in the TWA.
In 2001 and 2002 Osbourne appeared with Combat Zone Wrestling, where he feuded briefly with John Zandig despite a severely injured neck and arm.
In 2003 Osbourne pinned Christian York in a tournament final match to become the first Dynamite Championship Wrestling Heavyweight Champion and formed a stable with Riptide, The Bouncer and Johnny Thunder called The Pain Syndicate.
Osbourne's pursuit of the belt lasted nearly nine months and culminated in a three-way match with (then-champion) "Luscious" Johnny Graham and "Sexy" Shane Shadows.
The rivalry ended on June 9, 2007, with Osbourne defeating Cremator in a casket match during WPW's annual Summer Extravaganza card in Reading, Pennsylvania.