In 2000, Flair made her first appearances in professional wrestling at the age of 14, appearing with her father in World Championship Wrestling (WCW) as Ashley Flair during his feud with Vince Russo and her half-brother David. On the May 15 episode of Monday Nitro, Flair appeared in a vignette in which Russo, David and Daffney invaded the Flair family home until being confronted by Flair, her mother Beth, and her brother Reid. At The Great American Bash on June 11, Flair was at ringside for a retirement match between Ric and David. After Russo attempted to interfere in the match on David's behalf, she and her brother Reid attacked him and handcuffed him, enabling their father to go on to defeat David. On the following evening's episode of Monday Nitro, David and Russo faced Ric in a handicap match with the Flair family once again at ringside. Flair attempted to interfere on her father's behalf, but was restrained by R&B Security, Russo's henchmen, allowing David and Russo to defeat Ric and partially shave his head.
On May 17, 2012, she signed a developmental contract with WWE, joining NXT, the WWE developmental territory, in Tampa, Florida. Flair adopted the ring name Charlotte and had her first televised singles match on the July 17, 2013 episode of NXT, where she defeated Bayley. In late 2013, Charlotte formed a tag team with Bayley, and the two defeated Aksana and Alicia Fox on the September 4 episode of NXT. On the October 10 episode of NXT, Bayley accompanied Charlotte to a match against Santana Garrett, which she won, but during the match The BFFs—Beautiful, Fierce Females (Sasha Banks and Summer Rae) came to the ring and attempted to convince Bayley to join them, much to Charlotte's annoyance.
On the November 13 episode of NXT, Charlotte attacked Bayley and joined the BFFs, establishing herself as a villainess in the process. After a two-month absence due to a legit injury, Charlotte returned on the January 8, 2014, episode of NXT and began accompanying Rae and Banks to their matches. In February, Charlotte confronted and challenged NXT Women's Champion Paige during an interview with Renee Young. Following Rae's elevation to WWE's main roster, Charlotte and Banks went on to feud with Bayley, who formed an alliance with Natalya, who defeated Charlotte by disqualification after Banks interfered on the March 27 episode of NXT. On April 6 at WrestleMania XXX, she appeared alongside Sasha Banks and Alexa Bliss in Triple H's entrance in his match against Daniel Bryan. The feud between Charlotte and Paige ended on the April 24 episode of NXT, when Charlotte and Banks defeated Emma and Paige, with Charlotte scoring the pinfall over Paige.
In early May, Charlotte competed in an eight woman tournament for the vacant NXT Women's Championship, defeating Emma in the first round, Alexa Bliss in the semifinals, and Natalya in the finals at NXT TakeOver on May 29, 2014, to win the NXT Women's Championship for the first time in her career, her first championship win in the WWE. After a four-month absence from the show, Summer Rae returned on the June 6 episode of NXT, distracting Bayley and allowing Charlotte to defeat her, after which the BFFs attempted to attack Bayley, only to be chased away by Emma and the returning Paige. The altercation prompted a six-woman tag team match on the June 12 episode of NXT, which the BFFs lost after Bayley pinned Charlotte. On the July 3 episode of NXT, Charlotte got a measure of retribution over Bayley in a tag team match, where she and Sasha Banks defeated Bayley and Becky Lynch. After the match Charlotte left Banks to get attacked by Bayley, with Banks officially disbanding the BFFs in a backstage segment later that night.
On the July 24 episode of NXT, Charlotte successfully defended the women's championship against Summer Rae. Charlotte then went on to retain against Bayley at NXT TakeOver: Fatal 4-Way on September 11, after which she stopped Banks from attacking Bayley afterwards, and after defeating Bayley in a rematch on October 2 episode of NXT, she raised Bayley's arm before they shared a hug and shook hands, thus turning Charlotte back into a fan favorite character. Following this, Charlotte and Bayley feuded with Banks and her partner Becky Lynch throughout the following several weeks. Charlotte made her first appearance on WWE's main roster on the Slammy Awards special episode of Raw on December 8, where she lost to Natalya in a non-title match. Charlotte retained the NXT Women's Championship against Banks at NXT TakeOver: R Evolution on December 11, and in rematches that took place on the December 25 and the January 21, 2015, episodes of NXT, respectively. At NXT TakeOver: Rival on February 11, Charlotte dropped the championship to Banks in a fatal four-way match that also involved Bayley and Becky Lynch, ending her reign at 258 days. She failed to regain the championship in a rematch against Banks that took place on the March 4 episode of NXT.
At NXT TakeOver: Unstoppable on May 20, Charlotte teamed up with Bayley to defeat Emma and Dana Brooke. After defeating Emma and Brooke again on the July 8 episode of NXT, this time teaming with her rival Sasha Banks, Charlotte challenged Banks to an NXT Women's Championship match, which Banks accepted. They had their championship match the following week on the July 15 episode of NXT, in which Banks retained the championship, and afterwards the two shared a hug and Banks raised Charlotte's hand as a sign of respect.
On the July 13, 2015, episode of Raw, Stephanie McMahon called for a "revolution" in the Divas division, subsequently introducing Charlotte, Becky Lynch, and Sasha Banks as members of the main roster. Charlotte and Lynch allied with Paige, who was engaged in a feud with Team Bella (Alicia Fox and The Bella Twins), while Banks allied with Tamina and Naomi, starting a rivalry between the three teams. The trio of Charlotte, Lynch, and Paige was dubbed Team PCB after the first name initials of each wrestler. On July 19 at Battleground, Charlotte defeated Banks and Brie Bella in a triple threat match in her WWE pay-per-view debut. The three teams would ultimately face off at SummerSlam in a three team elimination match, which Charlotte's team won after Lynch pinned Brie Bella.
On the August 31 episode of Raw, Charlotte overcame fellow Team PCB members' records in the first ever Divas Beat the Clock challenge, and was named the new number one contender to Nikki Bella's Divas Championship. Her title match against Nikki Bella, initially advertised for Night of Champions, took place on the September 14 episode of Raw, so Charlotte could stop Bella from surpassing AJ Lee's record and becoming the longest-reigning Divas Champion. Charlotte won the match by disqualification after she pinned Brie due to the twins switching places, causing Nikki to retain her title and beat the record in the process. On September 20 at Night of Champions, Charlotte defeated Nikki in a rematch to win the Divas Championship for the first time. During Charlotte's celebration the following night on Raw, Paige cut a worked shoot promo and turned on her and Lynch, berating them and the Divas division. Throughout October, Paige acted as if she wanted to reconcile with Lynch and Charlotte, only to attack them both and cement her departure from the team, just a night after Charlotte successfully retained her championship against Nikki Bella at Hell in a Cell. In the end of 2015, Charlotte successfully defended her title against Paige on three different occasions—at Survivor Series on November 22, in a rematch the following night on Raw and at TLC: Tables, Ladders & Chairs on December 13.
In November, Charlotte began displaying villainous traits after defeating her friend Becky Lynch by feigning a leg injury, followed by a distraction provided by her father. Throughout December, the relationship between Charlotte and Lynch continued to strain, and after losing to her on the January 4, 2016 episode Raw, Charlotte attacked Lynch and solidified her villainous turn in the process for the first time since 2014 in NXT. Charlotte successfully retained the Divas Championship against Lynch with help from her father three days later on SmackDown, and at the Royal Rumble on January 24. In February, after she lost to her in a non–title match, Brie Bella received a title match at Fastlane, where Charlotte once again successfully retained her title. A few weeks later, on March 12 at Roadblock, Charlotte retained the title against Natalya. Also in March, Charlotte caused a number one contender's match between Lynch and Banks to end in a no contest after she attacked both contenders. As a result, a triple threat match between Charlotte, Banks and Lynch for the Divas Championship was scheduled for WrestleMania 32. At the event, a new WWE Women's Championship replaced the Divas Championship and Charlotte defeated Banks and Lynch to become the inaugural champion.
Right after WrestleMania 32, Charlotte began a feud with Natalya, successfully defending the title against her on the April 11, 2016 episode of Raw. Due to the disqualification ending, a rematch took place at Payback on May 1, where she defeated Natalya after referee Charles Robinson ended the match as Charlotte held Natalya in the sharpshooter, even though Natalya had not submitted, making reference to the infamous "shoot screwjob" the Montreal Screwjob. After the match, both Natalya and Bret Hart, who was in Natalya's corner, applied the Sharpshooter on Charlotte and Ric Flair. At Extreme Rules on May 22, Charlotte retained her title against Natalya in a submission match after a distraction provided by Dana Brooke who was dressed as Flair. The following night on Raw, Charlotte turned on her father by claiming she no longer needed him, further aligning herself with Brooke who would be dubbed as her protege. At Money in the Bank on June 19, Charlotte and Brooke defeated Natalya and Lynch in a tag team match. On the June 20 episode of Raw, Charlotte retained her title over Paige with help of Brooke, with the two attacking Paige after the match, which ended with Banks making the save. This led to a tag team match the following week, where Banks and Paige scored the victory. On July 24 at Battleground, Charlotte and Brooke were defeated by Banks and the debuting Bayley.
After being drafted to the Raw brand as part of the 2016 WWE draft on July 19, Charlotte made her first appearance for the brand on the July 25 episode of Raw, where she lost the WWE Women's Championship to Sasha Banks, ending her reign at 113 days. On August 21 at SummerSlam, Charlotte competed against Banks in a rematch for the title, in which Flair was victorious, thus becoming a two-time champion. At Clash of Champions on September 25, Charlotte retained the title (which had been renamed Raw Women's Championship after the creation of the SmackDown Women's Championship) in a triple threat match against Banks and Bayley. However, Charlotte dropped the title to Banks once again in the main event of the October 3 episode of Raw. Around this time, Charlotte's ring name was lengthened to Charlotte Flair.
At Hell in a Cell on October 30, Flair regained the title from Banks in the first ever women's Hell in a Cell match to become a three-time women's champion. This was also the first time a women's match was the last match on a WWE pay-per-view. The following night on Raw, Flair was revealed as captain of Team Raw for Survivor Series on November 20, where Team Raw defeated Team SmackDown with Flair and Bayley being the survivors for Team Raw. On the November 28 episode of Raw, Flair competed against Banks in a falls count anywhere match, where Banks defeated Flair for the title, after which Ric Flair came out and celebrated with Banks. A 30-minute iron man match between the two was scheduled for Roadblock: End of the Line on December 18, which resulted in a 2–2 draw, but Flair defeated Banks 3–2 in sudden death overtime, becoming a record four-time Raw Women's Champion as well as ending their six months feud since it was stipulated that Banks could not invoke her rematch clause after that. Shortly after, Flair started a feud with Bayley who managed to defeat her in two non-title matches since her main roster debut in August. This led to a title match between the two that took place at the Royal Rumble on January 29, 2017, where Flair successfully retained the title over Bayley.
On the February 13 episode of Raw, Flair dropped the title to Bayley in the main event. She later failed to regain the title in a rematch against Bayley at Fastlane on March 5, marking her first pay-per-view singles match loss after 16 singles victories. Also in March, Flair ended her association with Brooke and defeated her in a singles match. On April 2, at WrestleMania 33, Flair competed in a four-way elimination match against Bayley, Banks, and Nia Jax, being the last woman eliminated by eventual winner Bayley. On the April 10 episode of Raw, Flair was defeated by Jax in her final match for the brand.
On April 11, 2017, Flair was moved to SmackDown brand as part of the Superstar Shake-up. The following week on SmackDown Live, she defeated SmackDown Women's Champion Naomi in a non-title match, to earn a title opportunity, which ended in a no-contest after The Welcoming Committee (Natalya, Carmella and Tamina) attacked both contestants. This match made Flair the first woman in WWE history to ever compete in the main events of Raw, SmackDown and a WWE pay-per-view. In May, Flair aligned with Becky Lynch and Naomi against The Welcoming Committee, turning face in the process. The two teams faced off in a six-woman tag team match at Backlash, where The Welcoming Committee was victorious when Lynch submitted to Natalya's sharpshooter. Shortly after, Flair competed at Money in the Bank, as part of the first ever women's Money in the Bank ladder match, which was won by Carmella. On July 23, at Battleground, Flair competed in a five-way elimination match to determine the number one contender for the SmackDown Women's Championship, but she was the last woman eliminated eventual winner Natalya.
After an almost two-month hiatus due to her father's legitimate health condition, Flair made her return on the September 19 episode of SmackDown, thanking the WWE Universe for her family's support. Later that night, in the main event, Flair won a fatal four-way match to become the number one contender for the SmackDown Women's Championship. On October 8, at Hell in a Cell, Natalya retained her title over Flair as she attacked her with a steel chair, causing a disqualification victory for Flair. However, Flair received her rematch and defeated Natalya to win the championship in her hometown on the November 14 episode of SmackDown, becoming the first woman's wrestler to win the Divas, NXT, Raw, and SmackDown Women's Championship. With the win, Flair replaced Natalya in the interbrand champion vs. champion match against Raw Women's Champion Alexa Bliss on November 19 at Survivor Series which Flair won. A month later, at Clash of Champions on December 17, Flair retained the title against Natalya in a lumberjack match.
Towards the end of 2017, Flair once again aligned with Becky Lynch and Naomi to feud with the debuting Riott Squad (Ruby Riott, Liv Morgan and Sarah Logan), after the three attacked them shortly after their debut. Ruby Riott then challenged Flair to a title match at Fastlane on March 11, 2018, where Flair once again retained the SmackDown Women's Championship. After the match, the inaugural women's Royal Rumble winner Asuka came to confront her and challenged her to a title match at WrestleMania 34, which Flair won after she submitted Asuka, ending her undefeated streak at 914 days in the process. Two days after later, on the April 10 episode of SmackDown, The IIconics (Peyton Royce and Billie Kay) attacked Flair while she was cutting a promo and Carmella subsequently used her Money in the Bank opportunity to defeat Flair and win the championship, ending her reign at 147 days. Flair received her rematch against Carmella the following month, on May 6 at Backlash, but she failed to regain the title. In June, Flair competed in her second Money in the Bank ladder match, which was ultimately won by Alexa Bliss. After the event, Flair took a hiatus after undergoing a ruptured breast implant surgery.
After a short hiatus due to surgery, Flair made her return on the July 31 episode of SmackDown, saving her friend Becky Lynch from an attack by Carmella, and later defeating her to be inserted into her championship match with Carmella at SummerSlam, thus making it a triple-threat match. At the event, Flair defeated Becky Lynch and Carmella after she pinned Lynch to win the SmackDown Women's Championship for a second time in her career. With the win, Flair became the second woman in WWE history to ever hold seven women's championships, alongside WWE Hall of Famer Trish Stratus. After the match, Lynch would attack Flair, igniting a feud between the two, which would lead to a match at Hell in a Cell on September 16, where Flair lost the title to Lynch, ending her reign at 28 days. Flair defeated Lynch via disqualification at Super Show-Down and fought her in a rematch two days later, on the October 8 episode of SmackDown, which ended in a double count-out after Flair speared Lynch through the LED board. As a result of this, Flair received another title opportunity against Lynch in the first Last Woman Standing match at Evolution, in which Lynch defeated Flair.
In November, Flair was picked by Becky Lynch as her replacement in a match against Raw Women's Champion Ronda Rousey at Survivor Series, where she lost via disqualification after brutally attacking Rousey with a kendo stick and a steel chair. The following month, on December 16 at the TLC pay-per-view, Flair competed in the first ever women's Tables, Ladders, and Chairs match against both Lynch and Asuka, who would go on to win the match after Rousey interfered and pushed both Flair and Lynch off a ladder. On January 27, 2019, at the Royal Rumble, Flair competed in her first women's Royal Rumble match, where she lasted 50:01 minutes and eliminated five women, tying the eliminations record set by Michelle McCool in 2018, before becoming the last woman eliminated by Lynch who ultimately won the match in the process.
In February, Vince McMahon replaced Lynch with Flair in Lynch's title match against Ronda Rousey for the Raw Women's Championship at WrestleMania 35 after he suspended Lynch for 60 days in storyline. In March, Lynch was reinstated and she defeated Flair at Fastlane via disqualification, after Rousey purposely attacked Lynch to give her the win, making the title match at WrestleMania a triple threat match. Just a few weeks before WrestleMania, on the March 26 episode of SmackDown, Flair defeated Asuka to win the SmackDown Women's Championship for a third time, becoming the only woman in WWE history to have won eight women's championships. At the event, in what was the first time that women main evented a WrestleMania event, Flair lost her championship in a winner takes all for both her SmackDown and Ronda Rousey's Raw Women's Championships when Lynch pinned Rousey to win both titles. Shortly after WrestleMania, Flair continued her feud with Lynch over the SmackDown Women's Championship, as she implied that she had not been pinned or submitted to lose her title, and went onto defeat Bayley to earn herself a rematch for the title at Money in the Bank. At the event, which took place on May 19, Flair won the championship from Lynch after an interference by Lacey Evans who attacked Lynch with a Women's Right. After the match, the two continued to attack Lynch until Bayley making the save. Bayley, who had won the Money in the Bank briefcase, cashed-in on Flair and defeated her to end her reign at just 4 minutes and 52 seconds, Flair's shortest title reign of all time. Shortly after the Money in the Bank, Lynch was moved to the Raw roster and that officially put an end to the almost year-long feud between the two.
After a brief hiatus, Flair, once again working as a villainess, returned on the July 16, 2019, episode of SmackDown Live, defeating Liv Morgan. A week later, Flair, calling herself "the greatest female superstar of all time", was entered in a short storyline with WWE Hall of Famer Trish Stratus that led to a match between the two at SummerSlam. At the event, Flair was able to submit Stratus in what was the latter's legit retirement match. With her win over Stratus, Flair felt she deserved an opportunity at the SmackDown Women's Championship at the next month's Clash of Champions event and challenged reigning champion Bayley, who accepted. At the event, Bayley defeated Charlotte under dubious circumstances. After she submitted Bayley during a tag team match (between Flair and Becky Lynch against Bayley and Banks), Flair earned herself a rematch which took place on October 6, at the Hell in a Cell event, where Flair defeated Bayley to win her record fifth SmackDown Women's Championship and record tenth women's championship on WWE's main roster. Five days later, on SmackDown, Flair dropped the title back to Bayley.
As part of the 2019 Draft, Flair was drafted back to the Raw brand, thus ending her feud with Bayley. On the October 28 episode of Raw, Charlotte teamed with Natalya in defeating The IIconics. At the TLC pay-per-view in December, she teamed with Becky Lynch to challenge The Kabuki Warriors (Asuka and Kairi Sane) for the WWE Women's Tag Team Championship in a Tables, Ladders, and Chairs match, but the two were unsuccessful. On January 26, 2020 at the Royal Rumble pay-per-view, Flair entered the women's Royal Rumble match at number 17 and went on to win the contest by eliminating Shayna Baszler. Flair spent weeks teasing an announcement regarding her championship opponent at WrestleMania 36, leading to confrontations with NXT Women's Champion Rhea Ripley on Raw and NXT. At the NXT TakeOver: Portland pay-per-view event on February 16, after Ripley retained her championship against Bianca Belair, Flair attacked Ripley from behind and accepted Ripley's challenge to face her for the NXT Women's Championship at WrestleMania 36, and later attacked Belair. At the event, Flair defeated Ripley to capture her second NXT Women's Championship, marking her overall twelfth women's title in WWE. At NXT TakeOver: In Your House, Flair lost the title to Io Shirai in a triple threat match, also involving Rhea Ripley, ending her reign at just 63 days. In late June, after an attack by Nia Jax that led to a kayfabe injury, Flair was written out off television to take some time off to undergo another surgery.
On December 20, 2020, at the TLC: Tables, Ladders & Chairs pay–per–view, after a six months hiatus, Flair returned to WWE (once again as a face) revealing as the surprise tag team partner of Asuka, with whom she defeated Nia Jax and Shayna Baszler to win the WWE Women's Tag Team Championship. With the win, Flair became the fifth Women's Triple Crown Champion and fourth Women's Grand Slam Champion. However, Flair and Asuka would lose the tag team titles back to Jax and Baszler at the Royal Rumble, due to interference from Ric Flair and Lacey Evans. On the same night, Flair competed in the Women's Royal Rumble match, entering at number fifteen, however, she was eliminated by both Rhea Ripley and the eventual winner Bianca Belair. On the February 15 episode of Raw, after Lacey Evans announced she was pregnant, the Raw Women's Title match between her and Asuka at Elimination Chamber was cancelled and so was the storyline between her father and Evans. On the February 22 episode of Raw, Flair told her father to go home because she could not concentrate on her matches, marking the end of their storyline. After Flair defeated Shayna Baszler on the March 1 episode of Raw, she wanted to challenge Asuka for the Raw Women's Championship at WrestleMania 37, but that did not happen due to Flair being unable to compete, removing her from the WrestleMania title picture. On the April 12 edition of Raw, Flair returned as a heel for the first time since 2017, interfering in the title match for the Raw Women's Championship between Asuka and Rhea Ripley, attacking both. A week later, she would be out of action again, this time with the reason of being suspended on the April 19 episode of Raw for assaulting a referee, after losing to Asuka in a singles match. Her suspension would be lifted a week later on Raw by Sonya Deville. Charlotte would also be inserted into the Raw Women's Championship match in a triple threat match against Asuka and Rhea Ripley at WrestleMania Backlash, which was won by Ripley. At Hell in a Cell, Flair was once again unsuccessful in defeating Ripley. Finally at Money in the Bank, Flair defeated Ripley to win the Raw Women's Championship for a record-tying fifth time. However, she lost the title the next night on Raw against Nikki A.S.H., who cashed her Money in the Bank briefcase. On August 21, at SummerSlam, Flair regained the championship by defeating Nikki A.S.H. and Rhea Ripley in triple threat match.
As a part of the 2021 WWE Draft, Flair was drafted to SmackDown as Raw Women's Champion. On the October 22 episode of SmackDown, Flair and Lynch exchanged their titles, thus Flair became SmackDown Women's Champion for the record sixth time. On November 8, it was announced that Flair would face Raw Women's Champion Becky Lynch at Survivor Series, where she would be defeated. On February 4, 2022, Ronda Rousey made her SmackDown debut and officially challenged Charlotte for the SmackDown Women's Championship at WrestleMania 38. At the event, Flair defeated Rousey. Rousey then challenged Flair to a rematch at WrestleMania Backlash, this time in form of an "I Quit" match, which Flair declined, but was later made official. At the event, Flair lost the title to Rousey after shouting "I Quit".
After a seven-month hiatus, Flair returned as a face on the December 30 episode of SmackDown, challenging Ronda Rousey to an impromptu match for the SmackDown Women's Championship. Despite interference from Shayna Baszler, Flair defeated Rousey to win the title for a record-setting seventh time. This made her a fourteen-time women's world champion. At WrestleMania 39, on night one, Flair lost the SmackDown Women's Championship to 2023 Royal Rumble winner Rhea Ripley, ending her reign at 92 days. On the June 9 episode of SmackDown, Flair returned after a two-month hiatus and challenged Asuka to a match for the WWE Women's Championship, which Asuka accepted. Three weeks later on June 30, the match ended in a disqualification after Bianca Belair attacked both Asuka and Flair. At SummerSlam on August 5, Flair failed to win the title in a triple threat match after Belair pinned Asuka to regain the title, ending Flair's undefeated SummerSlam streak. At Fastlane, Flair failed to win the title in a triple threat match against Asuka and defending champion Iyo Sky after the referee was distracted by Sky's Damage CTRL stablemate Bayley and did not see Flair forcing Asuka to submit. On the October 20 episode of SmackDown, Flair failed to win the title from Sky after interference from Bayley and Dakota Kai. At Survivor Series WarGames on November 25, Flair, Belair, Becky Lynch and Shotzi defeated Damage Control (Bayley, Sky, Asuka and Kairi Sane) in a WarGames match. On the December 8 episode of SmackDown, Flalr suffered a knee injury during her match against Asuka. The following week, it was announced that Flair would be out of action for approximately nine months due to the injury.