Falkinburg ran a nightclub in Fort Myers, Florida called "Norma Jeans" (known for its Pink Cadillac) while he was working as a wrestling manager in the American Wrestling Association (AWA). He started managing 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, Falkinburg also managed Colonel DeBeers, Curt Hennig and Madusa Miceli as the leader of the Diamond Exchange stable. He worked for the AWA at 12 dates over a period of nine months, where they filmed all the television shows in one day.

Falkinburg also worked as a color commentator in Florida Championship Wrestling (FCW), soon renamed Professional Wrestling Federation (PWF), where he worked alongside Gordon Solie, before finally debuting as a professional Wrestler. Falkinburg's first pro match occurred in May 1989 against Dick Slater.

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 his pink Cadillac. At this time, he was virtually unknown in the World Wrestling Federation. When FCW went out of Business, Falkinburg was still involved in the club Business until Dusty Rhodes returned to World Championship Wrestling. Rhodes started booking and brought Falkinburg in on a small contract in early 1991.

On December 1, 1991, Page married Kimberly. On July 3, 2004, they announced their amicable separation.

Falkinburg continued wrestling and brought other Wrestlers into his stable, The Diamond Mine, such as Scotty Flamingo (Raven) and Vinnie Vegas (Kevin Nash). The relationships between DDP, Flamingo, and Vegas were used in many angles over the following months. Falkinburg 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 Falkinburg who filled Flamingo's glove with water. The following year, after Studd and Flamingo left the stable, Falkinburg teamed with Vinnie Vegas as the Vegas Connection. However, the team was disbanded shortly after its debut when Falkinburg suffered a torn rotator cuff in a match against Tex Slazenger and Shanghai Pierce toward the end of 1992 and was later fired, while Nash left WCW for the World Wrestling Federation.

Falkinburg returned on the edition of May 18, 1996, of WCW Saturday Night as a tweener defeating Billy Kidman. On May 19, Falkinburg participated in the Lord of the Ring Tournament (Battle Bowl) at Slamboree. Falkinburg was victorious when he defeated The Barbarian with two Diamond Cutters. The winner was to be the number one contender for the 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 Nash and 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" (a worked shoot) 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 the 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.

Page developed a yoga fitness program initially called Yoga for Regular Guys Workout or YRG after recovering from ruptures to his L4/L5 discs in 1998 and discovering the health benefits of yoga through his former wife, Kimberly. His favorite kind of yoga (according to his "Yoga for Regular Guys" book published in 2005) is "Power Yoga," an American-style version of "Ashtanga Style" yoga. Page worked with Doctor of Chiropractic Dr. Craig Aaron, the "Yoga-Doc" and developed the Yoga for Regular Guys Workout.

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.

His book, Positively Page, was released on February 5, 2000.

His return televised match was on November 3, 2001 at Rebellion losing to Big Show. After the Alliance lost at Survivor Series DDP along with the rest of the alliance members bar Test kayfabe lost their jobs.

Page became the WWF European Champion on the edition of January 31, 2002 of SmackDown, when he defeated Christian, a former follower of his positive "philosophy." At WrestleMania X8, Page retained the title in a rematch. However, he lost the title to william Regal on an episode of SmackDown that aired March 19. At age 46, he had nagging injuries, including a neck injury he suffered in a match with Hardcore Holly on the April 18, 2002 episode of SmackDown, so his WWF contract was allowed to expire.

In 2003, he had his name legally changed to Dallas Page.

On April 1, 2004, Diamond Dallas Page announced his return to the ring. After working for several independent promotions, he debuted with Total Nonstop Action Wrestling on November 12, feuding with Raven and Erik Watts. At Turning Point, DDP defeated Raven, and at Final Resolution (2005), Page competed in a three-way elimination match which was won by Monty Brown. On the February 4 edition of Impact!, Page and Monty Brown defeated The Naturals, then on the February 11 edition, Page defeated Chris Candido. At Against All Odds, Page and Brown defeated Team Canada (Bobby Roode and Eric Young). Page received an NWA World Heavyweight Championship title shot on March 13, 2005 at Destination X, but was defeated by reigning champion Jeff Jarrett when Monty Brown turned heel and hit Page with the Pounce. On the March 18 edition of Impact!, Page and Sean Waltman defeated Lex Lovett and Buck Quartermain, and on April 15, Page and Waltman faced The Outlaw and Monty Brown in a losing effort. At Lockdown, DDP teamed with B.G. James and Waltman to defeat Jeff Jarrett, Monty Brown and The Outlaw in a Lethal Lockdown match. At Hard Justice, Page and Ron Killings faced Monty Brown and The Outlaw where they were defeated in what was Page's final match in TNA. Page left TNA shortly thereafter.

On August 9, 2009, Diamond Dallas Page made a special appearance with JCW aligning himself with the jWo. He hit his trademark Diamond Cutter finisher on Trent Acid late in the match. Page retired from the ring shortly thereafter.

Page is commonly associated with the "Self High Five" as well as the "Diamond Cutter" symbol, a hand gesture made by joining the thumbs and index fingers on each hand to form a Diamond shape, then parting the two hands in one swift motion. He created the symbol in 1996 and later trademarked it. In December 2005, Page filed a lawsuit against Rapper Jay-Z, who, he claimed, had "illegally adopted his trademark hand gesture". Page accused Jay-Z of trademark infringement, and sought a prohibitive injunction and monetary damages. It resulted in Page dropping the lawsuit for an undisclosed amount of money. On August 31, 2010, Page filed a lawsuit against American electronica musical duo 3OH!3 for infringement of his trademarked "Diamond Cutter" hand gesture.

In late 2010, Page agreed to work on a DVD for WWE, titled The Very Best of WCW Monday Nitro, after being approached on the project due to his ties to WCW. Page hosted the DVD, which was released on June 7, 2011. On the June 27 edition of Raw, Page made an appearance promoting this DVD with Booker T.

Page developed the book into a series of workout videos titled DDP YOGA (formerly YRG). DDP Yoga was featured in a video about Arthur Boorman in May 2012. The story was picked up by the mainstream media, including Good Morning America. The video describes the journey of Arthur Boorman, a disabled war veteran who was told by doctors he would never walk again. After 15 years on crutches, Boorman lost 140 pounds in 10 months and regained the ability to walk and run without his crutches, back braces or leg braces.

On February 21, 2014, Page appeared on the ABC series Shark Tank, where he was seeking $200,200 for a 5% share in the company. He declined to sell a 50% share for that same amount. He had hoped to use the money to develop a mobile app. The Investors believed the company's profits ($800,000 in the previous year) would fall. Page later said he sold more than $1 million worth of product in the first six days after his appearance.

In an August 2014 New York Times article, Page was described as being engaged to a woman named Brenda Nair of Smyrna, Georgia. They married in Cancun on July 25, 2015. Page has two daughters, Brittany Page (born 1987) and Kimberly Page (born 1994). and two stepdaughters, Alexandra Nair (born 1996) and Rachel Nair (born 2001)

In 2016 Page was featured on the Nine Legends Expansion Pack to talk about his friend Bill Goldberg.

On March 31, 2017 Page was inducted into the WWE Hall of Fame in Orlando, Florida.