Anderson was a promising winger with good work-rate and pace when he came in exchange for John Welsh from Hull on New Years' Day 2006. Anderson was released by WBA as an under-16 player and wrote to Hull for a trial. After impressing at Tigers' academy Rafa Benítez snapped him up. Anderson was a key player in the Liverpool u-18 team that won the 2006 FA Youth Cup. That season he was on the bench for a Champions League last 16 tie at home to Benfica and was an unused substitute again the following season away at Galatasaray.

Anderson was loaned out to Swansea in the 2007/08 season where he scored seven goals when Swansea were promoted to the Championship and was voted the club's Young Player of the Year. Anderson was on loan at Nottingham Forest, who had been promoted alongside Swansea, in the 2008/09 season. He appeared in 28 of Forest's first-team matches, scoring two goals, but received a very nasty injury during an FA Cup-tie with Derby County in January 2009, breaking an arm and dislocating a wrist. But Forest liked what they saw of the player who had helped them battle successfully against relegation. Swansea were also interested and the two clubs made similar bids of around £250,000. In the end it was the East Midlands club that secured Anderson on a three-year contract on the last day of June 2009.

Anderson played in 39 Championship matches for Nottingham Forest in 2009/10 including both legs of the end-of-season play-off semi-final with Blackpool, which Forest lost 6-4 on aggregate. Anderson made a similar contribution in the following campaign as Forest again reached the end-of-season play-offs, but were beaten by Swansea on aggregate at the semi-final stage. Ironic, given that Anderson preferred Forest over the up-and-coming Swansea. Following Billy Davies' departure, Anderson felt new boss, Steve Cotterill, didn't believe in him as an out-and-out winger and he only appeared in 16 championship matches for Forest in 2011/12, partly due to injury. The East Midlands club had a difficult season but eventually recovered to finish in nineteenth. Anderson wasn't offered a new deal and joined Bristol City on a free transfer in August 2012.

Anderson made thirty first-team appearances for Bristol City in the 2012/13 season, scoring three times. He signed a two-year contract with Ipswich Town during the summer transfer-window of 2013 and when that expired dropped a division to League One, joining Bradford City. He was released in the summer of 2016 and then joined Northampton Town in League One. After a season there he dropped down a division again, joining Mansfield Town where he was a regular, but put up for sale at the end of the campaign. No offers were forthcoming and after failing to make a single appearance in the first half of the 2018-19 season, his contract was terminated by mutual consent on 31 January 2019. He signed a short term contract with Plymouth but was limited to just four substitute appearances.

After being without a club at the start of 2019/20, Anderson agreed to rejoin former club Northampton in October 2019. He made eighteen League Two appearances in a season that was curtailed due to Covid 19. Northampton finished in the play off positions on points per game and Anderson came on as a late substitute in the 4-0 victory to Exeter in final at Wembley, his first appearance at the national stadium. However, a few days later he was advised that he would not be offered a new deal. Anderson set himself up as a private football coach in Leicestershire and joined non league Melton Town for 2021/22, who were competing in the United Counties League Premier Division North, part of English football's ninth tier. Anderson combined playing there with part time coaching at Derby County and running a property development business. He continued playing for Melton in 2022/23, appearing 36 times whilst working towards his UEFA coaching A Licence. For 2023/24 he remained registered as a player at Melton but didn't make any appearances, instead focusing on his roles as assistant manager as well as coach of the Under 15's at Derby County. At the end of the season Anderson announced that he was bringing his playing career to an end so that he could focus on coaching higher age groups.