During 2005 and 2006, Young made several appearances for World Wrestling Entertainment (WWE) on its weekly programs Sunday Night Heat and Velocity as well as in dark matches on SmackDown and Raw.
On February 16, 2010, it was announced that he would compete as part of the first season of WWE NXT, mentored by CM Punk.
On February 23, 2010, Young made his debut on NXT with a character described as a "South Beach Party Boy", losing his debut match to David Otunga. His storyline had mentor CM Punk showing apathy towards him, claiming he had no idea why he's in NXT and did not want to train Young unless he accepted his straight-edge lifestyle. Despite this, Punk and his disciples, Luke Gallows and Serena, helped Young win his rematch against Otunga the following week. Young was ranked eight in the first pros' poll. After the pros' poll, Young decided to join The Straight Edge Society in an attempt to improve, only to change his mind before getting his hair shaved off. CM Punk decided to forgive him for standing up to him when he defeated Luke Gallows with Young's own hair on the line. Because of this victory, CM Punk had then been interested in Young's potential, but in turn started feuding with a jealous Luke Gallows. On May 11 in the second pros' poll, Young was ranked fifth out of the six remaining contestants and narrowly escaped elimination. The following week, however, Young was eliminated from the competition.
The week following the season one finale, Young, along with the other season one NXT rookies turned heel and interfered in the main event match on Raw between John Cena and Young's former Pro, CM Punk, and attacked both wrestlers, the announce team and the ring announcer Justin Roberts, and dismantled the ring area and surrounding equipment. On the June 14, 2010, edition of Raw, the rookies attacked General Manager Bret Hart, when he refused to give them contracts. The following week on Raw, Vince McMahon fired Hart and announced that a new General Manager had been hired, one that had signed all seven season one NXT rookies to contracts. The following week, the group was named The Nexus. On the July 5 episode of Raw, The Nexus tried to attack John Cena as he confronted Wade Barrett during their "truce" with one another. The segment ended with The Nexus leaving without Young, when other Raw wrestlers arrived to aid Cena, and Young was assaulted by Cena to end the show. Due to Cena's actions, the new general manager booked Cena in a 7-on-1 handicap match against The Nexus scheduled for the following week. Young did not participate due to injuries caused by Cena the previous week but The Nexus won the match. He returned at Money in the Bank with the rest of The Nexus, sporting a new haircut and costing Cena the WWE Championship against Sheamus. After the match, Cena attacked Young and fellow Nexus teammate, Michael Tarver. The Nexus continued to feud with Cena and the Raw roster, resulting in a seven-on-seven elimination tag team match at SummerSlam. Young was the first person to be eliminated from the match, when he submitted to Daniel Bryan in under a minute, and The Nexus lost the match. On the next episode of Raw, the members of The Nexus fought in individual matches against members of the victorious Team WWE with the stipulation that losing a match would have them exiled from the group. Young chose to face John Cena, but failed to win and was exiled and attacked as a result.
Young returned on the September 6 episode of Raw, distracting Barrett and costing him a match against Randy Orton, thus turning Young face. On the October 4 episode of Raw, Young participated in a battle royal to determine the number one contender to the WWE Championship, but was eliminated by The Nexus. Young had his first singles match since leaving The Nexus on the October 7 episode of Superstars, losing to William Regal. Young had his first win in singles competition on the October 14 airing of Superstars, defeating Primo. Young teamed up with Yoshi Tatsu in a losing effort against The Usos in mid-November on two occasions. Young got his first victory of 2011 when he teamed with Primo, Yoshi Tatsu and David Hart Smith to defeat Zack Ryder, William Regal and The Usos on the January 13 episode of Superstars.
In March 2011, Young was selected as one of six former NXT contestants to return to the show in its fifth season, NXT Redemption. During this season, Young was mentored by Chavo Guerrero. In the season premiere, Young defeated Jacob Novak and won the first challenge to earn himself "redemption points". On the April 12 episode of NXT, Young attacked Titus O'Neil after their match and tried to attack O'Neil's pro Hornswoggle, but was stopped by Guerrero. He turned heel, when he attacked Hornswoggle, and later he and Guerrero faced O'Neil and different tag team partners on several occasions. On the April 19 edition of Redemption, Young faced Hornswoggle in single match. During their match, Chavo Guerrero gave Young a blindfold but In the end Hornswoggle won after a tadpole splash. On the May 3 edition of Redemption, Young lost to his Pro, Chavo Guerrero, with Hornswoggle as a special guest referee. On the May 10 edition of Redemption, Hornswoggle didn't appear on NXT and accused by Hornswoggle's rookie Titus O'Neil. The following week, It was revealed Chavo Guerrero kidnapped Hornswoggle and hid Hornswoggle in the box. Then, Guerrero and Young attacked Hornswoggle in the ring until O'Neil made a save. The feud was settled when Titus O'Neil and Darren Young faced each other in a no disqualitication match on the May 24 episode of NXT Redemption. The match ended with Titus O'Neil the victor after Hornswoggle interfered in a match in which O'Neil attacked Guerrero and Young. Guerrero was later released from WWE, leaving Young on his own. In August, he formed an alliance with Derrick Bateman and the duo teamed up against O'Neil and NXT host Matt Striker, but were defeated. Young then moved into a feud with Striker, defeating him on two consecutive occasions. After Young attacked Striker following a handshake, William Regal intervened, saving Striker. Two weeks later, Young was defeated by Regal in a singles match. Young then formed an alliance with JTG and defeated Striker and O'Neil. After the match they were attacked by the Usos.
Young was suspended for thirty days on October 5, 2011. Following his suspension, Young returned on the November 16, 2011, episode of NXT and assaulted Titus O'Neil. Young was then able to get the better of O'Neil twice in tag team matches. The conclusion to Young's feud with O'Neil came when O'Neil defeated Young in a no disqualifications match.
O'Neil then turned heel and formed an alliance with Young. Young and O'Neil feuded with Percy Watson and Alex Riley in February 2012, defeating them twice. In March, while he and O'Neil were feuding with the Usos, Young started chasing the affections of Tamina.
On the April 18 episode of NXT, Young and O'Neil were signed by John Laurinaitis to the SmackDown brand. The team made their debut for the brand on the April 20 episode of SmackDown with a victory over the Usos. The team suffered their first team loss against the WWE Tag Team Champions Kofi Kingston and R-Truth on the May 18 edition of SmackDown. At the No Way Out pay-per-view in June, Young and O'Neil teamed up to defeat Justin Gabriel and Tyson Kidd, Primo and Epico, and the Usos in a four-way number one tag team match to earn a future shot at the WWE Tag Team Championship, after A.W. turned on his clients, Epico and Primo. On the July 16 episode of Raw, Young and O'Neil unsuccessfully challenged Kofi Kingston and R-Truth for the WWE Tag Team Championship. On the August 10 episode of SmackDown, they defeated Primo and Epico in a number one contenders match via disqualification when A.W. provoked Kingston and R-Truth, who were on commentary, into interfering in the match. That same day, A. W. was released from his contract. The Prime Time Players received their title shots at SummerSlam, but were again defeated by Kingston and R-Truth. On the September 7 edition of SmackDown, The Prime Time Players defeated Primo and Epico and The Usos in a triple threat tag team match to earn another shot at the title. But on Raw three days later, the Prime Time Players lost their title shot to the team of Daniel Bryan and Kane (soon to be known as Team Hell No). At the Survivor Series pay-per-view, Young took part in a 10-man elimination tag team match, but was eliminated by Rey Mysterio. Young also competed in the 2013 Royal Rumble, entering at entrant 15, but was quickly eliminated by Kofi Kingston.
On the August 19, 2013, edition of Raw, the Prime Time Players turned face in a winning effort against the Real Americans (Jack Swagger and Antonio Cesaro). The team gained a push, challenging for the WWE Tag Team Championship, but lost a match to the Shield. The duo also sided with other face wrestlers from the active roster, only to get punished by COO Triple H for preventing Daniel Bryan from being critically injured by Randy Orton. The Prime Time Players were amongst the select few ordered to battle The Shield in separately sanctioned 3-on-1 handicap matches on the September 20 edition of SmackDown, as punishment for their intervention.
On the January 31, 2014, episode of SmackDown after Young was pinned in a tag team match against RybAxel (Ryback and Curtis Axel), O'Neil attacked him and disbanded the team. On SmackDown the following week, Young attacked O'Neil backstage after his interview. Young picked up a victory over Damien Sandow on the February 14 edition of SmackDown before being attacked by O'Neil, which turned into a brawl and left O'Neil in tattered clothes. They fought at Elimination Chamber, with the victor being O'Neil. However, Young defeated O'Neil in a rematch on Main Event. At WrestleMania XXX, Young competed in the André the Giant Memorial Battle Royal, where he was eliminated by 3MB. At a WWE live event on April 12, Young was injured in a match against Fandango, and on April 16, he underwent surgery to repair a torn ACL in his left knee that would take him out of action for four to six months.
On the January 5, 2015, episode of Raw, Young appeared with the rest of the WWE roster in the opening segment. His official return came on the February 16 episode of Raw, where Young and an unnamed independent wrestler, Kevin Kross, were scheduled to face The Ascension, but were attacked by them before the match, leading to Young's former tag team partner Titus O'Neil making the save. This turned O'Neil face again and the Prime Time Players reunited. On the February 23 edition of Raw, The Prime Time Players defeated The Ascension to hand them their first win as part of the main roster, only to then be attacked by the two. Young participated in the second annual André the Giant Memorial Battle Royal at WrestleMania 31, where he was eliminated by Ryback.
At Elimination Chamber, The Prime Time Players participated in the first ever tag team Elimination Chamber match for the WWE Tag Team Championship, where they were the last team to be eliminated by The New Day (Big E, Kofi Kingston and Xavier Woods). At Money in the Bank, the Prime Time Players defeated The New Day to win the titles. At Battleground, The Prime Time Players retained the title against The New Day but dropped the title back to The New Day on August 23 at SummerSlam in a fatal–four-way match, also involving The Lucha Dragons and Los Matadores. Young and O'Neil would invoke their rematch clause for the September 14 episode of Raw, which they lost.
Towards the end of 2015, O'Neil and Young began focusing on singles careers. Young teamed with Damien Sandow on the Royal Rumble 2016 kickoff show in a fatal four-way tag team match in a losing effort. On the February 2, 2016, taping of Main Event, the duo returned to team with The Usos to defeat the Ascension, Stardust and Tyler Breeze. At WrestleMania 32, Young entered the third André the Giant Memorial Battle Royal and came within the final three, before being eliminated by Kane.
On the May 5 episode of SmackDown, Bob Backlund agreed to be Young's life coach, in a campaign to "Make Darren Young Great Again". Throughout the next couple of months on Raw and SmackDown, various vignettes featuring Young and Backlund aired, with Backlund assuming the role of Young's life coach. In a "life lesson" segment on the July 4 episode of Raw, Backlund approved of Young adopting his famous Crossface chickenwing. The week after on Raw, Young won an 18-man battle royal (after Apollo Crews and Baron Corbin eliminated themselves) to become the number one contender for The Miz's Intercontinental Championship at Battleground. The following week on Raw, Young defeated Alberto Del Rio, despite interference from The Miz. On July 19, Young, with Backlund, was drafted to the Raw brand as a result of the 2016 WWE draft. At Battleground, Young faced The Miz in a match that resulted in a double-countout after he applied the Crossface Chickenwing to Miz outside the ring to protect Backlund from Miz and Maryse.
Young began a feud with his former tag team partner Titus O'Neil on the August 1 episode of Raw. O'Neil questioned Young's motives on being "great again". Later that night, he defeated Young when he pinned him while grabbing Young's tights. Afterwards, he got into a backstage altercation with Backlund before Young came to the defense of Backlund by attacking O'Neil. The week after on Raw, Young defeated O'Neil by pinning him while grabbing O'Neil's tights, mimicking the way O'Neil defeated him. On the August 15 episode of Raw, Young and O'Neil seemingly reconciled and were placed in a match against The Shining Stars. During the match, O'Neil attacked Young with a Clash of the Titus, allowing The Shining Stars to win the match. Young would once again defeat O'Neil on the August 29 episode of Raw. After the match, he was attacked by O'Neil. Young teamed with Neville to defeat O'Neil and Curtis Axel on the September 16 episode of Superstars to culminate the feud.
In January 2017, Young suffered an arm injury while teaming with Sin Cara in a match against The Shining Stars. On October 29, 2017, Young was released from his WWE contract without him reappearing on television.