Born in Camden, London,[2] Jackson began his career at Tottenham Hotspur in 1999, signing professional terms in 2000; he continued to progressed through the reserve side.

[4] The 2003–04 season saw Jackson making his Tottenham Hotspur debut on 26 December 2003, where he started the whole game, in a 2–0 loss against Portsmouth.

However, he rarely broke into the first-team, making nine league appearances in the next two seasons and was released by Tottenham Hotspur in the summer of 2006.

[15] Jackson then went on loan to Colchester United, whom he would later join on a permanent basis and straight away made his debut for the club, in a 1–1 draw against Brentford on 11 March 2003.

[19] Jackson earned admiration while on loan at Coventry City when he scored the last-minute winning goal against local rivals West Bromwich Albion.

[23] Having appeared in a little role for the side and was considering returning to his parent club, he had his loan spell extended for another month following an injury of Brynjar Gunnarsson.

[25] From then on, Jackson had a handful of first team opportunities until he returned to his parent club after a three months loan spell that was completed in March 2005.

[31] After being released by Tottenham Hotspur in the summer of 2006, he was soon signed on a free transfer by Colchester, who were recently promoted to the Championship, and whom he had played for on loan in 2003.

[53] However, Jackson missed several games due to a back injury that was aggravated during the 1–1 draw against Milton Keynes Dons.

[65] Since making his debut, Jackson quickly established himself in the starting eleven at the club and found himself competition in central midfielders alongside Neal Bishop and Ricky Ravenhill.

[68] After returning to the first team from injury, he scored his second County goal came in the FA Cup against Bradford City on 7 November 2009.

[72] Following his loan spell at Charlton Athletic came to an end, Jackson recovered from a hamstring injury and returned to the first team as an unused substitute, in a 1–0 win over Northampton Town on 10 April 2010.

[76] On 18 February 2010 Jackson signed for Charlton Athletic on a one-month loan to cover at left-back following an injury to Grant Basey.

[78] However, he went on to make four appearances whilst on loan at Charlton Athletic before returning to his parent club after a hamstring injury ruled him out for six weeks.

[89] He then went on a goal scoring spree for the second time this season, which were against Brighton & Hove Albion,[90] Colchester United (twice),[91] Swindon Town[92] and Sheffield Wednesday.

[107] Despite suffering from injuries setback,[108][109][110] Jackson scored 13 goals in thirty–nine appearances in all competitions from left-midfield, as he led Charlton to the League One title, in which he described this as his favourite football moment.

[113] Manager Chris Powell praised Jackson's role to his leadership to help the club gain promotion to the Championship.

[125][126][127] After returning to the first team from injury,[128] Jackson then scored his first goal for the club on 9 November 2013, in a 4–2 loss against Leeds United.

"[130] After serving a three match suspension, Jackson then scored again, just coming on as substitute in the 80th minute, in a 1–1 draw against Ipswich Town on 1 January 2014.

[132] He later regained his first team place following his return from injury[133] and added two goals to his tally against Queens Park Rangers[134] and Watford.

[139][140][141] On his last game of the season against Brentford on 14 February 2015, which saw them win 3–0, Jackson revealed that he played through the pain of a cracked rib before being substituted by the second half.

[143] He made his first appearance since February, where he set up one of the goals, in a 4–1 win over Dagenham & Redbridge in the first round of League Cup.

[144] Four days later, on 15 August 2015, Jackson made his 200 appearances for Charlton Athletic, coming on as a later substitute, in a 1–1 draw against Derby County.

[154] Despite being on the substitute bench[155] and injuries,[156][157] his playing time was soon reduced because of this later in the season and the club were subsequently relegated to League One.

[164] Despite this, Jackson returned to the first team, but soon have his playing time reduced and appeared on the substitute bench for the rest of the season.

[171] His first appearance of the season came on 8 August 2017, where he started the whole game, in a 2–1 win over Exeter City in the first round of the League Cup.

[172] Although Chris Solly took up the captaincy in his absence throughout the season, Jackson occasionally appeared as captain in number of matches.

[181] Shortly after having his contract triggered for another 12 months at the end of the 2016–17 season, local newspaper Kent Live reported that Jackson was appointed as new first-team coach.

[191] On 8 February 2024, Jackson and assistant manager Terry Skiverton committed their long-term futures to the Dons, extending their contracts to 2026.

[197] He's married and his wife gave birth to a baby daughter, as she was heavily pregnant at the time he joined Charlton Athletic in February 2010.