Early career (2018–2022) Matthews made his
professional wrestling debut on 9 February 2018, under the
ring name Joe Bailey. Throughout 2019 and 2020, Bailey made appearances in
All Star Wrestling (ASW),
Progress Wrestling,
Westside Xtreme Wrestling (wXw), and
Evolve. In 2022, Matthews returned to Progress Wrestling, under his Charlie Dempsey ring name. He competed in the
Super Strong Style 16 Tournament, where he defeated Charles Crowley in the first round and was defeated by Chris Ridgeway in the quarterfinal. and began a feud with
Gallus, establishing himself as a
heel in the process. On the 18 November edition of
NXT UK, Die Familie defeated
Gallus in their first ever match as a team. Die Familie also started a feud with
A-Kid. On the 10 March 2022 edition of
NXT UK, Dempsey defeated A-Kid. Dempsey was later challenged by A-Kid to a
British Rounds Rules match. This took place on the 21 April edition of
NXT UK, where Dempsey won 2–1 in the sixth round. Dempsey competed in a tournament for the
NXT United Kingdom Championship, where he lost to
Oliver Carter in his final match for NXT UK.
NXT (2022–present) No Quarter Catch Crew (2022–2026) In August 2022, Dempsey moved to the
NXT brand. On the 14 February 2023 edition of
NXT, Dempsey started associating with
Drew Gulak, where Gulak served as a teacher for Dempsey. On the 18 April 2023 edition of
NXT, Dempsey challenged
Wes Lee for the
NXT North American Championship, which he lost. In the following months, Dempsey and Gulak formed
No Quarter Catch Crew (NQCC), where they would later be joined by
Myles Borne and
Damon Kemp. Throughout August and September, Dempsey competed in the
NXT Global Heritage Invitational to crown a #1 Contender for the
NXT Heritage Cup. Dempsey came up empty-handed as he lost to the likes of
Axiom (formerly A-Kid), Tyler Bate, and
Butch. On the 13 December 2023 edition of
NXT, Dempsey was involved in a
triple threat match for the NXT North American Championship with
Joe Coffey and the NXT North American Champion
Dragon Lee, who retained his title. On the 27 February 2024 edition of
NXT, Dempsey defeated
The Meta-Four's
Noam Dar 2–1 in a British Rounds Rules match to become the new NXT Heritage Cup Champion. At
NXT: Roadblock, NQCC announced that the NXT Heritage Cup will be defended by the whole stable under the "
Catch Clause". Under the Catch Clause, NQCC as a whole referred to themselves as the NXT Heritage Cup Champions but WWE only recognize Dempsey as the official champion. The Catch Clause was invoked on the 19 March episode of
NXT, with Gulak defeating
Chase University's
Riley Osborne 2–1 to successfully defend the Cup. On the 16 April episode of
NXT,
The D'Angelo Family leader
Tony D'Angelo revealed that his Family were hired by NQCC to (
kayfabe) eliminate Gulak. In reality, Gulak was written off following allegations from
Ronda Rousey that Gulak grabbed her pants' drawstrings backstage in 2022. Gulak subsequently left WWE on 3 May. D'Angelo demanded payment for the job but NQCC refused, causing a brawl between the two factions and resulting in a
six-man tag team match between the two factions at Week 1 of ''
Spring Breakin''', which was won by The D'Angelo Family (D'Angelo,
Channing "Stacks" Lorenzo and
Luca Crusifino). On the 7 May episode of
NXT, Dempsey and Borne faced Tyson DuPont and Tyrek Igwe in a tag team match. Before the match started, the match referee was declared "unavailable" and Stacks was announced as the
special guest referee, costing Dempsey and Borne the match through a fast count. After the match, an irate Dempsey gave D'Angelo a title shot at the NXT Heritage Cup as payment due to the D'Angelo Family and invoked the Catch Clause, which was nullified when D'Angelo and his Family kidnapped Kemp and Borne later that night. One week later, D'Angelo defeated Dempsey 2–1 to win the Cup, ending Dempsey's reign at 76 days. After the loss of the Cup, Dempsey declared that the stable needs structure and a chain of command and assumed a leadership role. He then ordered Kemp to face D'Angelo in a rematch for the Cup but Kemp lost the match 0–2 on the 4 June episode of
NXT. On the 13 August episode of
NXT, Dempsey defeated Tony D’Angelo 2–1 to win the NXT Heritage Cup for the second time after some outside interference from new stablemate
Wren Sinclair. On the 24 December episode of
NXT,
Lexis King, with Dempsey's father
William Regal as his cornerman, faced Dempsey in a rematch for the NXT Heritage Cup. Regal passed his
brass knuckles for King to use against Dempsey but King refused. Regal then punched King, to which the brass knuckles fell into the ring. The referee saw Dempsey pick up the brass knuckles and assumed that Dempsey used it on King and disqualified Dempsey. In British Round Rules, the Cup change hands upon disqualification of the reigning champion, resulting in King becoming the new NXT Heritage Cup Champion, ending Dempsey's second reign at 134 days. This is also the first instance of the NXT Heritage Cup changing hands due to disqualification. However, due to a grey area in British Round Rules on whether the Cup changes hand upon disqualification of the reigning champion, NXT general manager
Ava ordered King to return the Cup back to Dempsey and announced that they will compete for the Cup in a one-fall match at
NXT: New Year's Evil on 7 January 2025, where he lost the Cup back to King. WWE does not recognize this change. Following
NXT Battleground, Dempsey and the rest of No Quarter Catch Crew effectively turned
face due to the outpouring support for Myles Borne during his
NXT Championship match against
Oba Femi despite failing to win the title. On the 3 June episode of
NXT, Borne defeated Dempsey "British Rounds Rules" match, thus leaving No Quarter Catch Crew. It was meant to settle Borne's ambition to be a singles competitor independent of the group while Dempsey could test him in a match style that was in his favor.
BirthRight (2026–present) On the 10 March episode of
NXT, Dempsey reunited with Tavion Heights to face BirthRight (Lexis King and
Uriah Connors) in a tag team match. During the match, Dempsey attacked Heights and joined the BirthRight stable after the match, turning heel again. The stable consists of second generation WWE wrestlers–Dempsey as the son of William Regal; King as the son of
Brian Pillman; Connors as the son of
Fit Finlay; Channing "Stacks" Lorenzo and his fiancé
Arianna Grace, the daughter of
Santino Marella. At the
NXT Stand & Deliver countdown show on April 4, BirthRight teamed together for the first time where they lost to
Hank and
Tank,
Shiloh Hill,
EK Prosper, and Wren Sinclair in a 10-person mixed tag team match.
All Japan Pro Wrestling (2023–2024) Dempsey made his return to Japan with
All Japan Pro Wrestling (AJPW) on 31 December 2023, where he teamed up with
Yuma Anzai to face
Tatsumi Fujinami and his son LEONA in a winning effort. At AJPW's New Year Giant Series, Dempsey challenged
Katsuhiko Nakajima for the
Triple Crown Heavyweight Championship, which Nakajima won.
Total Nonstop Action Wrestling (2024) Dempsey made his
Total Nonstop Action Wrestling (TNA) debut on the 4 July 2024 episode of
TNA Impact! where he attacked
Leon Slater and
Trey Miguel during their match. After the attack, Miguel's tag team partner Zachary Wentz (who formerly wrestled on NXT as
Nash Carter), challenged Dempsey to a match. On the following week, Dempsey defeated Wentz in his TNA in-ring debut after interference from Myles Borne.
Game Changer Wrestling (2024) Dempsey made his
Game Changer Wrestling (GCW) debut at
GCW Josh Barnett's Bloodsport X on 4 April 2024, beating Matt Makowski by submission. He then made another appearance at Josh Barnett's Bloodsport XII on 24 November, defeating
Tracy Williams by
submission. == Other media ==