Youth career

Anderson began his professional career in the youth ranks of Crawley Town, joining in the summer of 2013. The midfielder spent a single season with the Red Devils before the youth team was disbanded and subsequently moved to Peterborough United in July 2014, joining the Under-18s.

Peterborough United

On 28 February 2015, Anderson made his first team as a late substitute in a 2–0 home win against Bradford City.^[4] He went on to make 10 appearances during the 2014–15 campaign, before signing a new contract to extend his stay with the club.^[5] Anderson was named Peterborough United Young Player of the Year.^[6]

He made a further five league and two cup appearances during the 2015–16 season, and recorded two assists against former club Crawley Town in a 2–0 victory in August.^[7] His final appearance of the season came on 17 October, with Anderson coming off the bench in a 1–1 draw with Port Vale.^[8]

Lincoln City

On 16 August 2016, Anderson joined National League club Lincoln City on a youth loan until 1 January.^[19] The move saw him reunited with manager Danny Cowley, who previously signed Anderson on loan at Braintree Town.^[20] He made his debut in a 1–0 defeat to Dagenham & Redbridge the same day with a 25-minute appearance from the bench.^[21] His first start for the club saw him record two assists in a 4–0 victory over Southport, before scoring his first goal in the subsequent 2–1 win at Macclesfield Town.^[22][23]

On 4 October, Anderson scored his second goal for the club in a 2–1 victory at Wrexham.^[24] He scored again four days later in a 1–1 draw at Bromley, before scoring his final goal for the club in a 5–2 win at Chester on 29 October.^[25][26] Not included in the squad to face York City on 22 November, Anderson was an unused substitute for the next two games before a final substitute appearance in a 2–1 victory over Tranmere Rovers on 17 December.^[27]

On 22 December, Anderson was recalled by Peterborough, amid interest from Football League clubs.^[28]

On 23 March, Anderson returned to Lincoln City on loan for the remainder of the season.^[29] The following day he marked his return with a substitute appearance in a 3–1 win over Forest Green Rovers.^[30]

On 20 July 2017, Anderson joined recently promoted League Two club Lincoln City for an undisclosed fee, signing a three-year contract.^[31][32] In July 2019 he signed a new contract.^[33] On the 4 June 2021, it was announced that he would be leaving at the expiration of his contract.^[34]

Bristol Rovers

On 13 July 2021, Anderson joined recently relegated League Two side Bristol Rovers on a two-year deal.^[35] On 2 October 2021, Anderson opened his account for the club when he gave his side the lead in an eventual 3–1 home defeat to Swindon Town.^[36] The season ended with a third career promotion for Anderson, a 7–0 thrashing of Scunthorpe United on the final day of the season seeing Rovers move into the final automatic promotion place on goals scored.^[37]

Having had a frustrating 2022–23 season due to injuries, Anderson underwent groin surgery in March 2023.^[38] With the winger due to be out on contract in the summer, he was linked with a number of League One and League Two clubs.^[39] In April 2023, having received a contract offer, it was revealed that club and player had reached an impasse.^[40] Following the final match of the season, manager Joey Barton admitted that they would not be offering the player a new contract on account of his injury record, instead offering him back to prove his fitness over pre-season.^[41] He departed the club at the end of the season.^[42]

Stevenage

On 16 June 2023, Anderson signed with League One side Stevenage.^[43] Having made just three appearances during the first half of the season, he joined Colchester United on loan until the end of the season in January 2024.^[44]