Roode would begin his career working a series of dark matches for World Wrestling Federation/World Wrestling Entertainment (WWF/WWE) between 1998 and 2004.
On April 1, 2016, Roode was shown on-screen standing in the crowd at NXT TakeOver: Dallas under the name Bobby Roode. On June 8 at NXT TakeOver: The End, Roode appeared backstage during an interview with NXT General Manager William Regal, where he was seen walking into Regal's office, hinting that Roode was about to sign with WWE or had already done so. On June 11 during NXT's tour in the United Kingdom at Download Festival, Roode made his in-ring debut and defeated Angelo Dawkins. On August 3, Roode made his NXT television debut and quickly turned on the crowd to establish himself as a heel. The following week on NXT, Roode appeared after Andrade "Cien" Almas defeated Angelo Dawkins and informed Almas that General Manager William Regal scheduled a match between the two on August 20 at NXT TakeOver: Brooklyn II, where Roode defeated Almas. On the September 14 episode of NXT, Roode defeated No Way Jose in his Full Sail University debut. On the September 28 episode of NXT, Roode appeared after Tye Dillinger defeated Angelo Dawkins and later persuaded Dillinger to be his tag team partner for the 2016 Dusty Rhodes Tag Team Classic. On the October 12 episode of NXT, Roode and Dillinger were defeated by SAnitY (Alexander Wolfe and Sawyer Fulton) in the first round after Roode walked out on Dillinger during the match. Roode and Dillinger attacked each other following their matches throughout the subsequent weeks, leading to a match on November 19 at NXT TakeOver: Toronto, in which Roode defeated Dillinger.
On the December 14 episode of NXT, Roode qualified for a #1 contender's fatal four-way match for the NXT Championship after defeating Oney Lorcan. On the December 21 episode of NXT, Roode defeated Andrade "Cien" Almas, Tye Dillinger and Roderick Strong in the fatal four-way match to earn the title shot against NXT Champion Shinsuke Nakamura. On January 28, 2017 at NXT TakeOver: San Antonio, Roode defeated Nakamura to win the title, becoming the oldest NXT champion in WWE history in the process. On the March 15 episode of NXT, Roode made his first successful title defense, defeating Kassius Ohno. On April 1 at NXT TakeOver: Orlando, Roode successfully defended the title against Nakamura in a rematch, giving Nakamura his first clean singles loss in his departing match from NXT. On the April 19 episode of NXT, Roode was interrupted by Hideo Itami, who attacked him with a GTS. On May 20 at NXT TakeOver: Chicago, Roode retained the NXT Championship against Itami. On the June 7 episode of NXT, Roderick Strong announced his intentions of capturing the NXT Championship and Roode came out to mock him. Sparking a rivalry, the two engaged in a backstage brawl two weeks later after Roode mocked Strong and his family. On the July 5 episode of NXT, Roode successfully defended the NXT Championship against Strong. On the July 19 episode of NXT, Drew McIntyre defeated Killian Dain, earning the right to challenge Roode for the NXT Championship. On the August 2 episode of NXT, Strong attempted to attack Roode during a backstage interview, in which Roode claimed to be a "better man" than Strong. On the August 16 episode of NXT, Roode attacked both McIntyre and Strong during their main event to end the show. On August 19 at NXT TakeOver: Brooklyn III, Roode lost the NXT Championship to McIntyre, giving Roode his first singles loss in NXT. On the August 30 episode of NXT, Roode lost to Strong in his last televised NXT match. Roode wrestled his NXT farewell match at a NXT live event in Toronto on September 9, when he defeated Velveteen Dream.
On the August 22, 2017 episode of SmackDown, Roode made his main roster debut as a face, defeating Aiden English in a singles match and later defeated Mike Kanellis on the following episode of SmackDown Live. On the September 26 episode of SmackDown Live, Roode confronted and challenged Dolph Ziggler for a match on October 8 at Hell in a Cell which Roode won with a roll-up whilst holding Ziggler's tights. Afterwards, Ziggler attacked Roode and demanded a rematch on the following episode of SmackDown Live which Roode accepted, suffering his first pinfall loss as this time it was Ziggler who was holding Roode's tights this time. On the October 24 episode of SmackDown Live, Roode interrupted a backstage interview with Ziggler and Renee Young, suggesting a two out of three falls match next week on SmackDown Live with Ziggler, which he accepted. Roode then defeated Ziggler two falls to one, ending their feud and also earning a spot on Team SmackDown at Survivor Series. On November 19 at Survivor Series, Roode was eliminated second overall by Braun Strowman and Team SmackDown then eventually lost to Team Raw. In late November, Roode started a rivalry with United States Champion Baron Corbin, leading to a match for the title on December 17 at Clash of Champions also involving Ziggler, who won the title by pinning Corbin.
On January 3, 2018, Roode was announced to team with SmackDown Women's Champion Charlotte Flair (dubbed The Robe Warriors) in the Mixed Match Challenge tournament. After Ziggler vacated the United States Championship on the December 19 episode of SmackDown Live, an eight-man tournament was set up to crown a new champion. Roode defeated Baron Corbin in the first round and Mojo Rawley in the semi-finals. On the January 16 episode of SmackDown Live, Roode defeated Jinder Mahal in the final to win his first championship since joining the main roster. Roode would defend the title for 54 days, retaining against Rawley during the Royal Rumble kick-off show during an open challenge and Rusev on the February 6 episode of SmackDown Live, until he lost it against Randy Orton at Fastlane, causing Roode to attack Orton out of frustration after saving him from Mahal. Roode tried to regain the title at WrestleMania 34 in a fatal 4 way match against Orton, Mahal and Rusev, which was won by Mahal. During this time, in the Mixed Match Challenge, Flair (who had to undergo a minor teeth surgery) was replaced by Becky Lynch via fan-vote on social media, and Roode and Lynch defeated Finn Bálor and Sasha Banks. Flair returned for the finals of the Mixed Match Challenge, which Roode and Flair lost to the team of The Miz and Asuka.
On April 16, Roode was moved to Raw as part of the Superstar Shake-up. In his Raw debut, he was unveiled as the surprise member of the ten man tag match in which he teamed with Bobby Lashley, Braun Strowman, Finn Bálor, and Seth Rollins in successful fashion as they faced off against The Miz, Bo Dallas, Curtis Axel, Kevin Owens, and Sami Zayn. At the Greatest Royal Rumble event, Roode performed in his first ever Royal Rumble match, lasting just under eighteen minutes before being eliminated by Baron Corbin. Roode's first rivalry on the Raw roster was with Elias, with the pair trading victories over the months of April and May. On the May 14 episode of Raw, Roode defeated Baron Corbin and No Way Jose to qualify for the Men's Money in the Bank ladder match at Money in the Bank on June 17, which was won by Braun Strowman.
On the September 3 episode of Raw, Roode started a partnership with Chad Gable and went on to defeat The Ascension. At Survivor Series, they would lead the Raw tag team division, but they would lose to Team SmackDown in a 10-on-10 Survivor Series tag team elimination match. After feuding with them for weeks, Roode and Gable defeated AOP (Akam and Rezar) and their manager Drake Maverick in a three-on-two handicap to capture the Raw Tag Team Championship on the December 10 episode of Raw, after Roode pinned Maverick. At TLC: Tables, Ladders & Chairs, Roode and Gable along with Finn Balor, Apollo Crews and Kurt Angle helped Braun Strowman defeat Baron Corbin in a Tables, Ladders, and Chairs match and Corbin was stripped of all authoritative power. Roode and Gable would go on to beat The Revival in title matches on December 24, 2018 episode of Raw and on the January 7, 2019 episode of Raw in a Lumberjack Match and then again on the January 21 episode of Raw with Curt Hawkins as the special guest referee.
At the Royal Rumble kick-off show, Gable and Roode defeated Rezar and Scott Dawson in a non-title match. The match stipulation stated that if Rezar and Dawson were to win, their respective teams (AOP and The Revival) would both receive tag team championship matches. The Revival would eventually receive their title match on the February 11 episode of Raw, in which Gable and Roode lost the championship. On the March 4 episode of Raw, Roode and Gable interfered in The Revival's match with Ricochet and Aleister Black, attacking both teams. At Fastlane, Roode and Gable competed in a triple threat tag team match for the Raw Tag Team Championship, which was won by The Revival.
At WrestleMania 35, Roode competed in the André the Giant Memorial Battle Royal, but was unsuccessful. The following night on Raw, after losing a tag team match to Ricochet and Aleister Black, Roode and Gable turned heel by attacking Ricochet. This would be Roode's first time as a heel on the main roster. On April 16, Chad Gable was drafted to SmackDown during the Superstar Shake-up, disbanding the team and leaving Roode on his own. On the April 22 episode of Raw, Roode, sporting a clean shave and moustache, formalized his name to Robert Roode, before defeating Ricochet. On the May 20 episode of Raw, Roode became the second holder of the WWE 24/7 Championship, pinning the inagural champion Titus O'Neil on the entrance ramp. His reign ended in the same night when R-Truth defeated him in the parking lot. At Super Showdown, Roode competed in the 51-Man Battle Royal where he was unsuccessful. On the June 20 episode of Main Event, Roode defeated Cedric Alexander. On the June 27 episode of Main Event, Roode, Cesaro and EC3 defeated Lucha House Party (Gran Metalik, Kalisto, and Lince Dorado). On the July 15 episode of Raw, Roode and The Revival lost to Ricochet and The Usos in a 2-out-of-3 Falls Six-Man Tag Team Match.
On the August 26 episode of Raw, Roode teamed with Dolph Ziggler to win a tag-team turmoil match to earn a Raw Tag Team Championship match against Seth Rollins and Braun Strowman at Clash of Champions, where they would win the tag titles. On the October 14 episode of Raw, Roode and Ziggler lost the titles to The Viking Raiders (Erik and Ivar) and they were drafted to SmackDown as part of the 2019 WWE Draft. The team later alligned themselves with Baron Corbin during his feud against Roman Reigns. At Survivor Series, Roode and Ziggler won a 10-team Interbrand tag team battle royal. On December 10, Roode was suspended for 30 days for violating of WWE's Wellness Policy. Roode returned on the January 10, 2020 episode of SmackDown, where he helped King Corbin and Ziggler beat down Roman Reigns and The Usos. On the January 17 episode of SmackDown, Roode lost a tables match to Reigns. Roode entered the Royal Rumble match at the namesake pay-per-view at number four, but was quickly eliminated by the WWE Champion Brock Lesnar. It was later announced that Roode and Ziggler would compete in a Elimination Chamber match for the WWE SmackDown Tag Team Championship at the Elimination Chamber event. On the March 6 episode of SmackDown, Roode and Ziggler won a tag team gauntlet match to enter the Elimination Chamber last. At the event, Roode and Ziggler eliminated Heavy Machinery, but then were eliminated by The Usos. Following Elimination Chamber, Roode was not seen on television as he wasn't able to travel due to the pandemic.
On the June 22 episode of Raw, it was announced that Roode and Ziggler were traded to the Raw brand. On the September 28 episode of Raw, Roode made his return and answered the open challenge from WWE Champion Drew McIntyre, where he failed to win the title. As part of the 2020 draft in October, both Roode and Ziggler were drafted back to the SmackDown brand. On the January 8, 2021 episode of SmackDown, Roode and Ziggler defeated The Street Profits (Angelo Dawkins and Montez Ford) to win the SmackDown Tag Team Championship. This would mark the team's first SmackDown Tag Team Championship, second tag team championship overall as a team, and Roode's third tag team championship as an individual. At WrestleMania SmackDown on April 8, Roode and Ziggler defeated Alpha Academy, The Mysterios and The Street Profits in a fatal four-way match to retain the titles. On the April 16 episode of SmackDown, Roode and Ziggler defeated The Street Profits to retain the titles. At WrestleMania Backlash, Roode and Ziggler lost the titles to The Mysterios, ending their reign at 128 days.
As part of the 2021 Draft, both Roode and Ziggler were drafted to the Raw brand. On the October 4 episode of Raw, Roode and Ziggler lost to Big E and Drew McIntyre. On the October 25 episode of Raw, Ziggler and Roode defeated Alpha Academy and the Street Profits in a number one contenders match for a Raw Tag Team Championship opportunity later that night; Roode and Ziggler failed to win the titles. On the November 1 episode of Raw, Roode and Ziggler defeated The Street Profits. At Survivor Series, Roode competed in a 25-man dual branded battle royal, which was won by Omos. At the Royal Rumble, Roode competed in the Royal Rumble match, where he was eliminated by AJ Styles. The night before WrestleMania 38, during the "WrestleMania edition" of SmackDown, Roode competed in the André the Giant Memorial Battle Royal, which was won by Madcap Moss.
On the June 6 episode of Raw, Roode and Ziggler returned to the brand for the first time in months where they appeared for an interview segment on the stage, but would be interrupted by Omos and MVP. Ziggler then superkicked MVP and both Roode and Ziggler were chased out of the arena by Omos, therefore turning Roode face for the first time since 2019. On September 29, it was reported that Roode underwent a procedure and would be out of action indefinitely.
In late August 2023, Roode began transitioning into a backstage producer role for the company.