Dickson started his career at
Erith & Belvedere before moving to
Dulwich Hamlet in the summer of 2006. He scored 31 goals in 36 games for Dulwich in the 2006–07 season. Dickson signed for
Charlton Athletic on 12 March 2007 from Dulwich Hamlet for £35,000, signing a two-and-a-half-year deal after scoring twice in a reserve-team game for Charlton. In the first half of the
2007–08 season, Dickson went out on loan to two
League One clubs. First he joined
Crewe Alexandra but failed to score in three games. Crewe declined an option to renew his loan, and he joined
Gillingham on loan in September 2007. His time at
Priestfield was far more productive, totalling 11 goals in 14 games, including a hat-trick on his full debut against
Luton Town. This goal haul was sufficient to make him Gillingham's top scorer that season, even though he was recalled to
The Valley in December 2007. He scored his first goal for Charlton in an
FA Cup third Round replay against
West Bromwich Albion, but shortly after was ruled out for the rest of the season due to injury. He signed a new two-year deal with Charlton in August 2008. Dickson began a three-month loan spell at
Bristol Rovers by scoring twice in a 3–1 win away at
Brentford on 19 September 2009, and went on to play 14 league matches for them. He returned to Gillingham for a second loan spell, also of three months, in February 2010. After an unsuccessful trial at
League Two side
Stevenage, Dickson joined
Nea Salamis Famagusta FC on a two-year contract. After winning the
Cypriot First Division and finishing as a runner up in the
Cypriot Cup with
AEL Limassol, for whom he also scored in the
Europa League against
Marseille, and
Shanghai Dongya, Dickson joined
League Two side
Dagenham & Redbridge on a free transfer, leaving in 2014. He subsequently spent three seasons playing in Cyprus, taking in spells at Pafos, Enosis Neon Paralimni and Ermis Aradippou. In the summer of 2016, Dickson returned to England, signing for
National League side
Sutton United. He made his full league debut in a 4–0 away defeat to
Chester on 27 August. On 9 December, Dickson was released by Sutton United having made nine full and 11 substitute appearances in the league, as well as two substitute appearances in the FA Cup, without scoring a goal. Dickson signed for
National League South side
Chelmsford City on 6 January 2017. He made his debut after coming on as a substitution against
Whitehawk and scored his first goals for the club when he scored twice against
Hemel Hempstead Town. One week later Dickson went on to score four goals against
Eastbourne Borough. Dickson joined
Hampton & Richmond Borough in July 2018, before moving on to
Hornchurch a year later. On 21 November 2020, Dickson joined
Dartford on dual registration terms and - on the same day - scored two goals on his debut against
Slough Town. Dickson briefly returned to Erith & Belvedere; the club where he started his career. On 26 October 2021, Dickson joined
Cray Wanderers. On 30 July 2022, Dickson joined
Billericay Town. On 30 December 2022, Dickson joined
Brentwood Town on a one-month loan deal. On 3 February 2023, Dickson rejoined
Hornchurch. In June 2023, Dickson returned to his first club, newly promoted Isthmian League South East Division side Erith & Belvedere. He made the step up a division to join
Chatham Town in November 2023. On 26 July 2024, Dickson joined
Horsham. On 28 December 2024, Dickson became the first senior footballer to score a hat-trick on his 40th birthday, in a 6-0 win over Potters Bar Town in the
Isthmian League. He departed the club at the end of the
2024–25 season following a title-winning campaign. In July 2025, Dickson joined Isthmian League South East Division side
Sittingbourne. Just three weeks after joining the club however, he departed by mutual consent, returning to Cray Wanderers. On 26 January 2026, Dickson left Cray Wanderers. On 13 March 2026, Dickson signed for
Cray Valley Paper Mills. ==International career==