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In 2003, Galloway made his debut for the inaugural show of British Championship Wrestling (BCW), operating in the Greater Glasgow area.
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In the FWA Academy, while he was trained by the promotion's operator Mark Sloan along with Justin Richards and James Tighe, Galloway also cites the promotion's established wrestlers helping out with training, including Doug Williams, Paul Burchill and Alex Shane.
The match was booked as an "I Quit" match with Conscience as the special guest referee with Galloway gaining his second BCW Heavyweight Championship.
After gaining momentum in Scotland, Galloway began wrestling dates across the Republic of Ireland with Irish Whip Wrestling (IWW) continuing to use "Thee" Drew Galloway as his gimmick.
On 15 October 2006, Galloway competed in Insane Championship Wrestling (ICW) debut show Fear & Loathing, defeating Darkside and Allan Grogan in a three-way 30-minute Iron Man match to become the first ICW Heavyweight Champion.
He held the title for 280 days, ultimately losing it to Darkside on 22 July 2007 in a five-man elimination match that also involved Jack Jester, Wolfgang and Liam Thomson.
He is a former two-time ICW World Heavyweight Champion with Insane Championship Wrestling and a former Evolve Champion, Open the Freedom Gate Champion and two-time Tag Team Champion with Evolve.
After his initial tenure with WWE ended with his release in June 2014, Galloway re-signed with the company in April 2017 back under his former ring name and joined the developmental brand NXT, first appearing at NXT Take Over: Orlando.
Their brutal and bloody Street Fight saw Galloway gain respect from for his tenacity and endurance With his rivalry against Manson settled in their Street Fight and despite having only won one match with the company, Galloway was given a shot at the IWW International Heavyweight Championship owing to his show stealing performances with Manson.
The rivalry quickly took on a patriotic flavour, with Galloway's blue colours of Scotland clashing O'Shaunessy's green colours of Ireland, mirroring the Old Firm football derby between Glasgow Rangers and Glasgow Celtic, respectively.
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