Sporting Fingal Following his schoolboy years at St Malachys FC and both
Belvedere and St. Kevin's Boys,
Dublin-born Dawson joined Sporting Fingal in 2009. Initially part of their Under–20 squad, Dawson forced his way into Fingal's first team picture making 4 appearances during the 2009 First Division season. Dawson won an FAI Cup winners medal in 2009 as an unused substitute during Sporting's Fingal's 2–1 victory over Sligo Rovers. Following Sporting Fingal's promotion to the Premier Division for 2010, the young midfielder made a further 16 league and cup appearances and won a
2010 A Championship Cup medal as part of their reserve side. Ahead of the 2011 season, Dawson was still under contract at Sporting Fingal but following the pre-season demise of the club Dawson was left without a club.
Shelbourne On 14 February 2011, Dawson was snapped up Shelbourne for their 2011 First Division campaign. He became more of a permanent fixture halfway through the season where he helped Shels gain promotion to the Premier League. He received praise for his performance in the 2011 FAI Cup Final against Sligo Rovers. Shelbourne would eventually lose on penalties, Dawson being one of the players to miss from the spot.
Yeovil Town Dawson signed for English
League One side
Yeovil Town following the expiry of his Shelbourne contract upon the opening of the 2013 January transfer window, signing a contract until the end of the 2012–13 season. On 8 January 2013, Dawson made his Yeovil debut as a substitute in their
Football League Trophy area semi-final defeat against
Leyton Orient. On 19 May 2013, Dawson played in the
2013 League One play-off final as Yeovil beat
Brentford 2–1 to secure promotion to the
Football League Championship. On 26 June 2013, Dawson signed a two-year contract extension.
Cheltenham Town On 17 May 2017, Dawson rejected the offer of a new contract at Yeovil, and signed for fellow League Two side
Cheltenham Town on a two-year deal.
Forest Green Rovers On 1 July 2019, Dawson rejected the offer of a new contract from Cheltenham Town to sign for
League Two rivals
Forest Green Rovers on an initial one-year deal. At the end of the 2019–20 season, Dawson was released by Forest Green Rovers.
Gloucester City On 10 September 2020, Dawson signed for
National League North club
Gloucester City.
Torquay United On 4 March 2023, Dawson joined
Torquay United on loan for the remainder of the season.
Gloucester City On 5 June 2024, Dawson returned to Gloucester City following their relegation to the
Southern Football League Premier Division South. ==Personal life==