On April 13, 1996, at Massacre on Queens Blvd, D-Von debuted in Extreme Championship Wrestling. Dudley feuded with the other members of The Dudley Brothers (his kayfabe half-brothers), claiming that their comedic antics were not the way true Dudleys should act, and faced Buh Buh Ray Dudley on numerous occasions, defeating him at Ultimate Jeopardy, but losing to him at November to Remember. Dudley eliminated Dances with Dudley, Dudley Dudley, and Chubby Dudley before joining forces with Buh Buh Ray, Big Dick Dudley, Sign Guy Dudley, and Joel Gertner. Known collectively as The Dudley Boyz, D-Von and Buh Buh Ray dominated the ECW tag team division, winning the ECW World Tag Team Championship a record eight times and defeating teams such as The Eliminators and The Gangstas. D-Von, Buh Buh Ray, and Gertner all achieved a degree of infamy for their vitriolic interviews, which antagonized audiences to a point of near riot.
In mid-1999, Bubba Ray and D-Von left ECW and debuted in the World Wrestling Federation (WWF) in September. Throughout 2000 and 2001, the Dudley Boyz engaged in a three-way feud for the World Tag Team Championship with the Hardy Boyz and Edge and Christian. The feud incorporated the first triangle ladder match at WrestleMania 2000, and two Tables, Ladders, and Chairs matches, the first at SummerSlam in August 2000 and the second at WrestleMania X-Seven. While they were initially villains and were known for driving women through tables, the Dudley Boyz became fan favorites in early 2000. In early 2001, they were joined by Spike Dudley. In late 2001, the Dudley Boyz won the World Tag Team Championship, which they unified with the WCW Tag Team Championship during The Invasion, a storyline where the wrestlers from World Championship Wrestling and Extreme Championship Wrestling invaded the WWF.
Following WrestleMania X8, the company divided the roster into two brands, Raw and SmackDown! in March 2002. The Dudley Boyz were separated when D-Von was drafted to SmackDown! and Bubba Ray ended up on Raw. D-Von became a villainous reverend character initially serving as Mr. McMahon's "spiritual advisor", and later alongside his protégé Deacon Batista. Though the gimmick was a launching platform for Batista's career, it didn't last long and D-Von was betrayed by Batista. He did pick up one of his most memorable individual victories of his WWE career when he pinned Triple H on May 9, 2002 on SmackDown! after Chris Jericho hit Triple H with D-Von’s collection box.
He eventually was reunited with Bubba Ray and Spike on November 17, 2002 at Survivor Series when he helped Bubba, Spike and Jeff Hardy defeat 3-Minute Warning and Rico in a tables match. The Dudley Boyz then became a stable in the Raw tag team division over the next sixteen months, feuding with teams such as 3-Minute Warning, La Résistance, and various combinations of The Un-Americans. They held the WWE World Tag Team Championship several more times before being traded (along with Booker T) to SmackDown! on March 22, 2004 in exchange for Triple H.
On May 27, 2004 the Dudley Boyz kidnapped Paul Bearer, the manager of Paul Heyman's enemy The Undertaker. On June 27, 2004 at The Great American Bash, The Undertaker defeated the Dudley Boyz in a handicap match. They also won the WWE Tag Team Championships one more time but were upset by the high-flying team of Paul London and Billy Kidman. In July 2004, the Dudley Boyz reunited with Spike. For the remainder of the year, they assisted Spike in his matches for the WWE Cruiserweight Championship.
In early 2005, the Dudley Boyz were removed from WWE television while the WWE creative team attempted to devise a storyline for them. The Dudley Boyz returned to WWE television in June 2005 in order to promote ECW One Night Stand, an ECW reunion show. In the weeks preceding One Night Stand they, along with several other ECW alumni, vied with former WCW President Eric Bischoff and his "anti-hardcore crusaders". At One Night Stand on June 12, the Dudley Boyz defeated Tommy Dreamer and The Sandman in the main event.
On July 5, 2005, WWE announced that it had opted not to continue contract renewal negotiations with the Dudley Boyz.
On the August 24, 2015 episode of Raw, he and Bubba Ray Dudley made a surprise return to the WWE, reviving their Dudley Boyz tag team persona. They attacked the WWE Tag Team Champions, The New Day, and gave a 3D through a table on Xavier Woods. On the August 27 episode of SmackDown, they defeated The Ascension and after the match, they put Viktor through a table. On the August 31 episode of Raw, they defeated The New Day. After the match they attempted to put Big E through a table with a 3D, but Kofi Kingston and Xavier Woods saved him. On the September 17 episode of SmackDown, D-Von quickly defeated Kofi Kingston in his first singles match in WWE since 2004, after a distraction by Woods. At both Night of Champions and Live from Madison Square Garden, the Dudleyz challenged The New Day for the WWE Tag Team Championship, but would win both matches by disqualification, which allowed The New Day to retain their titles. At Hell in a Cell, the Dudley Boyz would challenge for the titles again, where they would lose to The New Day. At Survivor Series, the Dudley Boyz would team with Goldust, Neville and Titus O'Neil to defeat Stardust, The Ascension, The Miz and Bo Dallas in a 5-on-5 Traditional Survivor Series Elimination Tag Team Match.
In December, the Dudley Boyz began a feud with The Wyatt Family, and later aligned themselves with the returning Tommy Dreamer and Rhyno in the feud, known as The ECW Originals. At TLC: Tables, Ladders and Chairs, The Wyatt Family defeated The ECW Originals in an 8-Man Elimination Tables Match. At the 2016 Royal Rumble kickoff, the Dudley Boyz, Mark Henry and Jack Swagger, The Ascension and Darren Young and Damien Sandow competed in a Fatal 4-Way Tag Team Match to qualify for the Royal Rumble match itself, in a losing effort.
On the February 8 episode of Raw, the Dudley Boyz attacked The Usos after a match involving them against The New Day and Mark Henry, thus turning heel in the process. Explaining that they did not come back to WWE to be a "nostalgia act" and reminding the fans that they are "the baddest tag team on the planet", the Dudley Boyz abandoned using tables. In the following weeks, the Dudley Boyz and The Usos began a feud, setting up a tag team match between the two teams at WrestleMania 32, where the Dudley Boyz lost to The Usos. The following night on Raw, the Dudley Boyz defeated The Usos in a tables match, breaking their vow to never again use tables and officially ending the feud. Afterwards, the duo were interrupted by the debuting Enzo Amore and Colin Cassady, who proceeded to insult them and ignite a new feud. In a tournament set up by Shane McMahon to determine the new number 1 contenders to the WWE Tag Team Championship, they would defeat The Lucha Dragons to advance to the semi-finals, where they clashed with Enzo Amore and Colin Cassady in a losing effort. On July 19 at the 2016 WWE draft, the Dudley Boyz were drafted to Raw. At SummerSlam, they would lose to Sami Zayn and Neville.
The day after SummerSlam, the Dudley Boyz announced that they were departing from WWE on that night's Raw. During their farewell segment, they were confronted by The Shining Stars. After receiving insults from The Shining Stars, the Dudley Boyz attacked them, turning face once again in the process. As they set up Primo for a 3D through a table, Luke Gallows and Karl Anderson attacked both Bubba Ray and D-Von, sending D-Von through the table.
On September 26, a month following his departure from the company, D-Von would return to WWE as a backstage producer. While mainly working backstage, D-Von occasionally appeared on WWE television to separate brawls between wrestlers. On January 22, 2018 on the occasion of Raw 25 Years, the Dudley Boyz returned for one night only, by interrupting a fight between Heath Slater and Rhyno and Titus Worldwide, giving a Dudley Death Drop to Heath Slater through a table. The Dudley Boyz were inducted into the WWE Hall of Fame Class of 2018. In July 2019 during the Raw Reunion, D-Von returned in a one-off appearance to be in the corner of The Revival in a tag team match against The Usos in a losing effort.
At NXT 2300 on November 6, 2024, Bubba Ray and NXT Champion Trick Williams lost to Ethan Page and Ridge Holland in a tag team match. After the match, Bubba Ray and Williams put Page through a table that was brought to the ring by D-Von, reuniting the Dudley Boyz in the process.