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Matthews debuted in 2000 but wrestled his first professional match for Impact Championship Wrestling during June 2001. As a New York native, Matthews has generally worked for promotions across the northeastern United States. During 2006, Matthews was signed to a developmental contract to World Wrestling Entertainment. Afterwards, Matthews continued his work on the independent promotions. He became a regular performer for Pro Wrestling Syndicate. In PWS, Matthews won his third PWS Heavyweight Championship on February 9, 2013 and remains the reigning champion. Matthews holds the current record of most title reigns as the PWS Heavyweight Champion.
- Finishing moves
- The Ego Driver (Powerbomb onto knees)
- Spinning Reverse STO
- "2 Cocky"
- Teams and stables
- Matthews Brothers with Greg Matthews
- The D-Factor with Alexa Thatcher, Alicia, Archadia, Becky Bayless, DJ Hyde, Havok, Jonny D, Monsta Mack and Rhino (as Kevin Matthews)
- Reality Check with Alexa Thatcher, Alex Reynolds, The Amazing Red, Craven Varro, Damian Gibbs, Danny Demanto, Dave Sturch, Devon Moore, Evil Starman, Jay Lethal, Kyle Reynolds, Shelly Martinez and Velvet Sky (as Kevin Matthews)
- PWS Heavyweight Championship (3-times), (current)