- Holly made his WWF debut in 1991, but became a regular three years later.
- In 1993, Holly was brought into Jim Cornettes now defunct Tennessee based Smoky Mountain Wrestling promotion.
- Holly competed in the 1994 Royal Rumble in Providence, RI, as Thurman “Sparky” Plugg, a racecar driver gimmick.
- He later became “Spark Plug” Bob Holly with the same gimmick.
- On January 22, 1995, Holly and the 1-2-3 Kid (X-Pac) defeated Bam Bam Bigelow and Tatanka in the tournament finals to capture vacant the WWF World Tag Team title at the 1995 Royal Rumble.
- The Intercontinental title was held up after an April 26, 1995 match between champion Jeff Jarrett and challenger Holly.
- On May 26, 1996, Holly pinned Isaac Yankem (Kane) at the “Beware of Dog” pay-per-view in Florence, SC.
- Enjoying only mild success, Holly spent some time away from the ring in 1997. He returned with a manager Jim Cornette, and a new tag team partner, Bart Gunn.
- Cornette dubbed Holly and Gunn the New Midnight Express.
- On March 30, 1998, the New Midnight Express defeated the Headbangers to win the NWA World Tag Team title in Albany, NY.
- At Unforgiven ’98, Holly and Gunn defeated The Rock-n-Roll Express.
- When the NWA/WWF angle finished, Holly joined Al Snows JOB Squad with the Blue Meanie, and Duane “Gillberg” Gill. Snow and Holly would eventually have a falling out.
- Following his departure from the JOB Squad, Bob became “Hardcore” Holly.
- Holly pinned Snow to win the vacant WWF Hardcore Title at the St. Valentine’s Day Massacre in Memphis, TN.
- At Wrestlemania XV in Philadelphia, Holly beat Snow and Billy Gunn in a “hardcore triangle” match to win the WWF Hardcore Title.
- Holly served as a special guest referee at Fully Loaded ’99 for the Kane vs. The Big Show contest.
- Erin O’Grady, an independent wrestler from California, was introduced as Hardcore’s “cousin.”
- At the 1999 No Mercy pay-per-view, Hardcore and Crash Holly beat The New Age Outlaws via disqualification.
- Brian Christopher, Scott Taylor, Hardcore and Crash Holly beat Christian, Edge, and the Hardy Boyz at the 1999 Survivor Series in Detroit.
- Hardcore and Crash Holly beat Viscera and Rikishi at the 1999 Armageddon.
- Hardcore Holly won a 13-man Hardcore battle royal at Wrestlemania 2000 in Anaheim, CA, to capture the WWF Hardcore title.
- At the June 27, 2000 “Smackdown” taping in Hartford, CT, Holly suffered a broken arm in a match with Kurt Angle.
- Holly returned to WWF television on November 13, 2000, following the WWF title match between Angle and Crash Holly on “Raw.”
- Later on the show, Hardcore teamed with Crash and the Undertaker to defeated Angle, Edge, and Christian.
- Holly upset Angle on the May 3, 2001 edition of “Smackdown” thanks to an outside distraction from Chris Benoit.
- On September 20, 2001, Holly had a steel plate surgically removed from his left arm.
- In September 2002, Holly suffered a ruptured disc in his neck which required surgery.
- At the 2003 Survivor Series, Team Angle (Angle, Benoit, Cena, Bradshaw and Hardcore Holly) defeated Team Lesnar (Lesnar, Matt Morgan, Nathan Jones, Big Show, and A-Train).
- At No Way Out ’04, Holly defeated Rhyno.
- After a serious staph infection, Holly recovered was moved from the Smackdown roster to ECW on August 21, 2006.
- Hardcore Holly was drafted by the Smackdown brand during the June 17, 2007 supplemental draft.
- On December 10, 2007 in Bridgeport, CT, Holly and Cody Rhodes defeated Trevor Murdoch and Lance Cade for the World Tag Team titles on “Raw.”
- WWE released Holly on January 16, 2009.