D-Von and Bubba Ray Dudley 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.
Following WrestleMania X8 the company divided the roster into two brands, Raw and SmackDown! in May 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 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!. He eventually was reunited with Bubba Ray and Spike on November 17, 2002 when he returned to Raw. The Dudley Boyz 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 Cruiserweight Championship. In early 2005, the Dudley Boyz were removed from WWE television. 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 superstars, vied with Raw General Manager 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.
After a 10 year absence from the company, D-Von and Bubba Ray Dudley returned on the August 24th 2015 episode of Raw by attacking the New Day and confronting the Prime Time Players. They made their in-ring return the following Thursday on SmackDown, where they defeated The Ascension. They had their first Raw match in over ten years on the August 31 episode, where they defeated The New Day, therefore putting them in contention for the tag titles. On the September 3 episode of Smackdown they defeated The Prime Time Players. On the September 17 episode of SmackDown, D-Von wrestled his first singles match in WWE since 2004, when he faced Kofi Kingston, where D-Von was defeated in a quick match after a distraction by Xavier Woods. At both Night of Champions and Live from Madison Square Garden, the Dudley Boyz challenged New Day for the WWE Tag Team Championship, but would win both matches by disqualification, which allowed New Day to retain their titles. At Hell in a Cell, the Dudley Boyz would challenge for the titles again, where they would be defeated by 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.
The following night on Raw, the Dudleys suffered a defeat against Bray Wyatt and Luke Harper of The Wyatt Family. On the November 26 edition of SmackDown, the Dudley Boyz faced the Wyatt Family again, beating Erick Rowan and Braun Strowman by disqualification after Harper attacked Bubba Ray and threw him through his own table. On the next Raw, they had a no-contest six man tag team match against Harper, Rowan and Strowman when the Dudleys teamed with the returning Tommy Dreamer. However, the Dudleys and Dreamer fended off a post-match assault and threw Wyatt into a table. At TLC: Tables, Ladders and Chairs, The ECW Originals were defeated by The Wyatt Family in an elimination tables match. The next night on Raw, the Dudley Boyz, Dreamer and Rhyno were defeated again by The Wyatt Family in an 8-man tag team Extreme Rules Match.
On the February 8 episode of Raw, D-Von and Bubba Ray attacked The Usos after a match involving them against The New Day and Mark Henry. On the following Smackdown, Bubba Ray cemented the team's heel turn by saying that The Dudley Boyz are the "baddest team on the planet", and returned to the WWE to add to their legacy. He further claimed that the fans think they are a nostalgia act, so they will no longer use tables; forcing officials to carry several of them to the backstage area. n 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 announcing their departure 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.