Page started managing in the American Wrestling Association (AWA) in 1988, where he handled Badd Company (Paul Diamond and Pat Tanaka), a team he led to the AWA World Tag Team Championship on March 19. Badd Company, was often accompanied by female valets known as the "Diamond Dolls" (Tonya, Jennifer and Torri). During his time in the AWA, Page also managed Colonel DeBeers, Curt Hennig and Madusa Miceli as the leader of the Diamond Exchange stable.
In 1990, Dallas received a tryout with the WWF as an announcer, but wasn't offered a job. At WrestleMania VI, he drove Rhythm and Blues (The Honky Tonk Man and Greg Valentine) to the ring in a pink Cadillac.
Page came to World Championship Wrestling (WCW) in 1991 as the manager of The Fabulous Freebirds (Jimmy Garvin and Michael P.S. Hayes). Page managed the Freebirds to a shot at the WCW World Tag Team Championship where they defeated Doom (Butch Reed and Ron Simmons) on February 24. Before that match took place, Page unveiled the stable's new road manager, Big Daddy Dink, formerly known as Oliver Humperdink, who interfered in the match. During this match, Page introduced the Diamond Dolls. Page added Scott Hall to the stable under the name of Diamond Studd. Dallas also worked as a color commentator for WCW with Eric Bischoff. He debuted as a wrestler in a tag team match later that year. With the Diamond Studd, he faced Kevin Sullivan and his partner. He was relegated to the "jobber" list. He made his wrestling pay-per-view debut at Starrcade in 1991, teaming with Mike Graham in a losing effort to Jushin Thunder Liger and Bill Kazmaier.
Page continued wrestling and brought other wrestlers into his stable, The Diamond Mine, such as Scotty Flamingo and Vinnie Vegas. The relationships between DDP, Flamingo, and Vegas were used in many angles over the following months. Page went in the corner of Scotty Flamingo at Clash of the Champions XXI on November 18, 1992, when Flamingo fought Johnny B. Badd in a worked boxing match. Flamingo won this bout with a little help from Page, who filled Flamingo's glove with water. The following year, after Studd and Flamingo left the stable, Page teamed with Vinnie Vegas as the Vegas Connection. However, the team was disbanded shortly after its debut when Page suffered a torn rotator cuff in a match against Tex Slazenger and Shanghai Pierce toward the end of 1992 and was later fired, while Vegas left WCW for the World Wrestling Federation.
After his injury had healed, Page returned to WCW television in 1994, with his wife Kimberly as the Diamond Doll, and an on-screen bodyguard, Max Muscle. He held open arm wrestling challenges to win Kimberly, but Max always helped him win or arm wrestled for him. He was also involved in an angle where he was said to have supposedly amassed the sum of 13 million dollars through victories in arm wrestling competitions, a fortune that he would later lose. He also had a long feud with Dave Sullivan because Sullivan gave Kimberly gifts (and largely because Page was defeated by Sullivan in one of the arm wrestling contests, which earned him a date with Kimberly). At Fall Brawl, Page won his first championship when he defeated Renegade for the WCW World Television Championship. In the build-up to his first title defense at Halloween Havoc, there was growing dissension between Page and Kimberly. Johnny B. Badd defeated Page for the TV title and again at World War 3 on November 26, winning Kimberly's freedom from DDP. At Uncensored on March 24, 1996, The Booty Man, with Kimberly as The Booty Babe, defeated Diamond Dallas Page in a Loser Leaves Town match.
Page returned on the May 18, 1996, episode of WCW Saturday Night as a tweener defeating Billy Kidman. On May 19, Page participated in the Lord of the Ring Tournament (Battle Bowl) at Slamboree. Page was victorious when he defeated The Barbarian with two Diamond Cutters. The winner was to be the number one contender for the WCW World Title which at that time was held by The Giant. However, he never received the title shot that he earned that night. Page was feuding with Eddie Guerrero when the New World Order (nWo) was formed. Since Kevin Nash and Scott Hall were both former partners of Page, they assisted him in his matches in the tournament being held for the vacant United States Heavyweight Championship. Believing their assistance was not appreciated, however, Hall and Nash attacked him during the tournament finals, therefore handing the belt to Guerrero. After demonstrating the benefits of the nWo, they asked him to join. He responded by giving them Diamond Cutters on January 25, 1997 at Souled Out, starting a face turn and a feud with the nWo. Soon after, Page began a feud with recent nWo recruit "Macho Man" Randy Savage. On an episode of Nitro, Savage, aided by Scott Hall and Kevin Nash, attacked Page and spray-painted "nWo" on his back. A few weeks later at Uncensored, Savage and Miss Elizabeth "broke" by revealing to the world that Page and Kimberly were, in fact, married. Savage then proceeded to beat up Page, ensuring a future match between the two. At Spring Stampede, in Page's first pay-per-view main event, he and Savage battled in a match where Page emerged victorious, but it was not the end of conflict between the two. A few months later at The Great American Bash, they squared off again in an anything goes, lights out match. The match ended with Savage defeating Page with help from (then) Tag Team Champion Scott Hall. At Bash at the Beach, Scott Hall and Randy Savage defeated Diamond Dallas Page and Curt Hennig. Curt Hennig, who Diamond Dallas Page had recruited personally to join WCW and team with him, turned on DDP during the match. Hennig defeated Diamond Dallas Page in a grudge match at Road Wild. At Fall Brawl, Page teamed with Lex Luger to defeat Scott Hall and Randy Savage in a no disqualification match. Page even dressed up as masked wrestler La Parka and beat Savage. Around this time, Page also started fighting nWo leader, Hollywood Hogan. Page and Savage battled for the last time at Halloween Havoc. The match was billed as a Las Vegas Sudden Death match, where Savage pinned Page after Hogan, dressed as Sting, came out and hit Page with a baseball bat in his already "injured" midsection, resulting in Savage picking up the win. On an episode of Nitro shortly after Halloween Havoc, Page fought Hogan, but was again beaten down by the nWo.
At Starrcade, Page won the United States Heavyweight Championship from Curt Hennig. The following year at Uncensored, Page defended the title in a triple threat, falls count anywhere contest against Chris Benoit and Raven, putting Raven through a table with a Diamond Cutter to retain the belt. Page later lost the title to Raven at Spring Stampede. Later in the year, Page tagged with Karl Malone against Hulk Hogan and Dennis Rodman at Bash at the Beach, losing due to interference. Page tagged with late night talk show host Jay Leno at Road Wild, where they defeated Hogan and Eric Bischoff.
At Fall Brawl, Page won the WarGames main event, and got a World title shot against the undefeated Goldberg at Halloween Havoc. Page did not win the match, but the match was voted WCW Magazine's "Match of the Year" 1998. Halloween Havoc ran slightly longer than expected resulting in a number of cable companies blacking out the end of the Hogan versus Warrior match and all of the DDP versus Goldberg contest. WCW decided to air the Goldberg versus DDP title bout in its entirety on the October 26 episode of Nitro, which proved immensely popular in the ratings and resulted in a ratings win for Nitro over Raw – the last win Nitro ever had. Despite this setback in the World title picture, Page rebounded this same following night of Halloween Havoc, on the October 26 episode of Nitro, with a win over Bret Hart to capture the United States Heavyweight Title. The two headlined the following month's World War 3, in a title match which Page won. Page lost the title to Hart on the November 30 episode of Nitro in a no disqualification match, when he was assaulted by The Giant.
Page became WCW World Heavyweight Champion in April 1999, at Spring Stampede when he defeated Sting, Hogan, and Ric Flair for the title in a four way dance with "Macho Man" Randy Savage as Special Guest Referee. Page pinned Flair after giving Flair the Diamond Cutter. Page began to have a change in attitude; fans quietly began to start booing Page and he quietly turned heel. During the match, Page knocked Goldberg out with brass knuckles and repeatedly struck his leg with a steel chair as it was propped against the ring stairs, then taunted the fans by saying "boo me now" repeatedly. He only stopped when Kevin Nash, an ally of Hogan's who was angry at Page for (kayfabe) injuring Hogan's knee during the match at Spring Stampede, came back from injury and chased him away.
On April 26, 1999, Page lost and regained his title in the span of two hours. Sting challenged him to defend his title in the first hour of that night's Nitro and defeated him to regain the title he had lost had a year earlier. This ended Page's reign at 15 days, but he gained an opportunity to get the title back ninety minutes later. Nash came to the ring and made a challenge for a four-way match for the title, and the just-dethroned Page joined defending champion Sting and Goldberg in the match. Page regained the world title by using a foreign object to hit Nash and take the win and regain the title without actually defeating the reigning champion. Nash became the number one contender shortly after and vowed to get revenge on Page for his friend Hogan, culminating in a match at Slamboree in May. Page originally retained the World Championship after Savage interfered and hit Nash, but the match was ordered to continue by Eric Bischoff and Nash pinned Page to win the title after a powerbomb. Page dropped out of the title picture shortly thereafter.
Shortly after Slamboree, Page entered into an alliance with fellow New Jersey-an Bam Bam Bigelow and won the WCW World Tag Team Championship from then champions Perry Saturn and Raven on May 31, thanks to Chris Kanyon turning heel on former ally Raven and costing the team the championships. Page, Bigelow, and Kanyon became known as the Jersey Triad and through their alliance with WCW "President for Life" Ric Flair took advantage of the Freebird Rule in their subsequent matches (meaning any combination of the three could defend the championship). The Triad held the titles until June 10, when Saturn and Chris Benoit (now stablemates in The Revolution) took the title from them. They regained the belts at The Great American Bash three days later, and lost them to Harlem Heat at Road Wild in August. Later that night, Chris Benoit defeated Diamond Dallas Page to retain the United States title. The group broke up shortly thereafter and Page began feuding with Hogan again, joining Sid Vicious and Rick Steiner in a team effort to take on Hogan, Sting, and Goldberg. Soon after that feud ended, Page turned into a face again and feuded with both Kanyon and Bigelow before the year ended.
In 2000, with WCW under new management, Page earned a shot at the vacant World Heavyweight Championship belt at Spring Stampede against Jeff Jarrett. In a surprise twist, Page's wife, Kimberly, turned on Page and helped Jarrett become the new World Champion. Page got the better of Jarrett on the April 24 episode of Nitro, where he defeated Jarrett in a steel cage match to become WCW World Heavyweight Champion for the third time, then lost the title to his tag partner, actor David Arquette, three days later on Thunder; the rules stated that whoever got the pin would win the title, and Arquette pinned Jarrett's partner, Eric Bischoff. Page attempted to win the title back at Slamboree later that month in a triple cage match against Arquette and Jarrett, but lost after Arquette hit him with a guitar. Page then entered a feud with Mike Awesome, who defeated him in an Ambulance Match at The Great American Bash after Kanyon turned on Page.
Page took some time off shortly after this, but returned in late 2000 as a full-time wrestler. After Page came back he formed a tag team with Kevin Nash called The Insiders, and the team won the Tag Team Championship on November 26 at Mayhem by defeating Perfect Event (Shawn Stasiak and Chuck Palumbo). The team was temporarily stripped of the titles but won them back at Starrcade defeating Stasiak and Palumbo again. Page and Nash lost the titles to Palumbo and Sean O'Haire at Sin in January and broke up shortly thereafter. After his tag team run, Page briefly feuded with the returning Kanyon, which saw Kanyon defeat Page at SuperBrawl Revenge, and Page defeating Kanyon the following night on Nitro, ending their feud. Page then moved into the World Championship picture again by facing Scott Steiner. Their feud hit a climax at WCW's final PPV Greed, which saw Page's final match in WCW as he passed out in Steiner's finisher, The Steiner Recliner.
When WCW was purchased by WWF owner Vince McMahon in 2001, Page made the jump over to the WWF. He debuted in the World Wrestling Federation (WWF) on the June 18, 2001 episode of Raw when he unveiled himself as the stalker of The Undertaker's wife, Sara. Page revealed he didn't care about Sara; he only did it to make an impact and wanted to take on the "biggest dog in the yard". At King of the Ring, he fought The Undertaker in an unsanctioned brawl that was never announced as an official match. On the July 5 episode of SmackDown!, Page competed against WCW Heavyweight Champion Booker T, but failed to win the title after a distraction from the Undertaker. On the July 9 episode of Raw, WCW owner Shane McMahon and ECW owner Paul Heyman joined together to create The Alliance, with former WCW and ECW alumni joining forces in an attempt to take control of the WWF. At the Invasion pay-per-view, Page formed part of Team Alliance alongside Booker T, Rhyno and The Dudley Boyz, defeating Team WWF, after Team WWF member Stone Cold Steve Austin turned on his team members mid-match.
Page and Chris Kanyon reunited on the August 6 episode of Raw when Kanyon helped Page attack The Undertaker backstage. Three days later on the August 9 taping of SmackDown!, Page and Kanyon defeated the APA to win the WWF Tag Team Championship. His feud with the Undertaker culminated when he and Kane defeated Page and Kanyon at SummerSlam on August 19, 2001 in a Steel cage match for the WWF Tag Team Championship, where Page got injured which kept him out of action until late October 2001.
While Page was injured, he developed a new gimmick in which he became a motivational speaker. The character involved Page constantly smiling and acting optimistic, with his trademark phrase "That's not a bad thing... that's... a good thing". His return televised match was on November 3 at Rebellion, losing to Big Show. After the Alliance lost at Survivor Series, Page, along with the rest of the Alliance members, kayfabe lost their jobs.
Page eventually returned as a face and won his job back by defeating Big Boss Man on the January 17, 2002 episode of SmackDown!. Page competed in the Royal Rumble match at the titular event on January 20 but did not win. Page became the WWF European Champion on the January 31, 2002 episode of SmackDown!, when he defeated Christian, a former follower of his positive "philosophy." At WrestleMania X8, Page successfully retained in a rematch against Christian. However, he lost the title to William Regal on an episode of SmackDown! that aired March 21. On March 25, Page was drafted to the SmackDown! brand as part of the 2002 WWF draft lottery.
On the April 18 episode of SmackDown!, he sustained a serious neck injury during a match with Hardcore Holly, after botching a superplex. After receiving opinions from multiple doctors, Page eventually announced his retirement in June 2002. He left the promotion soon after.
On the June 27, 2010 episode of Raw, Page made an appearance with Booker T. Page also appeared alongside Kevin Nash and X-Pac at the WWE Hall of Fame ceremony on March 31, 2012. On July 2, 2012, Page made an appearance on Raw, where he hit a Diamond Cutter on Heath Slater. He also appeared at Raw 1000, accompanied by other WWE Legends, during Slater's match with Lita.
On the January 6, 2014, episode of Raw, Page, along with a number of other legends, appeared on the show as part of its "Old School" theme. On April 5, Page inducted Jake Roberts into the WWE Hall of Fame.
On January 25, 2015, at the Royal Rumble, Page was a surprise entrant in the Rumble match, entering at number 14, where he would hit his finishing move, the Diamond Cutter, on Stardust, Bray Wyatt and Fandango from the top rope, before being eliminated by Rusev. At WrestleMania 32, Page competed in the Andre the Giant Memorial Battle Royal, but was eliminated by Konnor.
On March 31, 2017, Page was inducted into the WWE Hall of Fame in Orlando, Florida.