[3] Dawson began his career with Leicester City before moving to Mansfield Town in 2005, where he made 131 appearances in all competitions.

He started his career as a trainee at Leicester City,[4] having joined from the Dublin schoolboy team Portmarnock AFC.

[7][8] After suffering a sore thigh and shortly recovered in the pre–season,[9] Dawson scored on his debut against Stockport County in the opening game of the season on 6 August 2005.

[11][12][13] Despite suffering from a groin strain,[14] he finished his first season at Mansfield Town, making the total of 45 appearances and scoring once.

[15] In the 2006–07 season, Dawson continued to remain in the first team regular for the side and was very fortunate to avoid a red card in a 2–1 win over MK Dons on 8 August 2006 after he "was first booked just before the break for a foul and then appeared to be shown a second a minute from time after lengthy protests over referee Kevin Wright's decision not to award him a penalty.

Ahead of the 2007–08 season, Dawson signed a new one-year contract on 10 August 2007[7] and his handful of first team appearances resulted him being praised for his work rate by Manager Bill Dearden.

[4] While at the club, Dawson was considered "tough tackling midfielder" and "a constant performer for Stags in the centre of the park.

[33] Dawson made his Bury debut on 9 August 2008 on the opening day of the season with a 1–0 win over Brentford at Gigg Lane.

[34][35] Since making his debut for the side, Dawson quickly established himself in the first team, partnering with Brian Barry-Murphy in central midfield.

[37] After being suspended against Darlington in the Football League Trophy campaign for picking up his fifth yellow card this season,[38] Dawson returned to the first team[39] and it wasn't until on 6 December 2008 when he scored again, in a 1–1 draw against Macclesfield Town.

[46] However, in a 1–0 loss against Cheltenham Town on 12 September 2009, Dawson was at fault when he gave away the ball, leading opposition player Barry Hayles, who scored the winning and only goal for the side.

[48] Despite this, Dawson managed to fend off his mistake and scored his first goal of the season on 29 September 2009, in a 3–2 win over Crewe Alexandra.

[62] However, Knill conceded defeat in attempt to keep Dawson, as it was made clear that he wanted to leave Bury to play at the higher level.

[65] Upon joining the club, he was given a number 8 shirt ahead of the new season[66] and also became Leyton Orient's Captain, succeeding Stephen Purches.

[70][71] However, during 3–0 win over Bristol Rovers, in which he set up one of the goals, Dawson received a horror tackle from Carl Regan, resulted him being substituted, which he described it as "a leg-breaker.

[77] Despite suffering from another injury,[78][79] Dawson finished his first season at Leyton Orient, making the total of 50 appearances and scoring 2 times in all competitions.

[81] However, after suffering another injury,[82] Dawson continued to feature in the first team[83] and wasn't until on 17 December 2011 when he scored, in a 2–1 win over Notts County.

[85] In a 2–1 loss against Carlisle United on 7 January 2012, Dawson was substituted in the first half after a challenge from Jon-Paul McGovern, in what turned out to be his last appearance for Leyton Orient.

[92] Since returning from injury, Dawson established himself as a regular part of the first team and finished the rest of the season, making 12 appearances.

[93][94] In the 2012–13 season, Dawson continued to establish himself as a first team regular in the midfield position[95] and then scored his first Barnsley goal on 29 September 2012, in a 1–1 draw against Ipswich Town.

[96] Throughout December 2012, Dawson scored three times in six appearances during the month against Leicester City,[97] Millwall[98] and Blackburn Rovers.

[99] However, he suffered an ankle ligament damage after just playing 12 minutes and was substituted as a result, in a 1–1 draw against Ipswich Town on 19 January 2013.

[108] Two weeks later, on 14 September 2014, Dawson captained Barnsley for the first time in absence of Luke Steele, in a 3–2 loss against Nottingham Forest.

Dawson's statement came three days after the National Crime Agency ended his nine-month ordeal by confirming that the case against him has been dropped.

[124] Upon joining the club, Manager Keith Hill said of the move: "Stephen Dawson has got a lot of aggression and he's pedigree.

[135] It was announced on 20 May 2015 that he will join Scunthorpe United on 1 July on a two-year deal with an option of a further year on a free transfer.

[150] At the start of the season, he continued to be in the first team, having to kept himself fit in the club's pre–season tour[151] and was featured in every match until he suffered an injury in late–November.

[152] After returning to the first team from injury,[153] He then scored his first goal for Scunthorpe in a 3–2 win over future club Bury on 7 January 2017.

[162] In a 1–0 loss against Sunderland in the first round of the League Cup, he tore a knee cartilage[163] and was afterwards declared unfit to play for five months.