Loan spells with Swansea City and Nottingham Forest resulted in a permanent move to the latter for whom he made nearly 100 league appearances.

As a schoolboy he was attached to Leicester City but they declined to offer him a professional contract, believing he would never make the grade.

[3] Anderson was a regular in the Liverpool U-18 team which won the 2006 FA Youth Cup and his performances led some to compare him to Michael Owen.

[4] Anderson earned his first call-up to the senior team in March 2006 when he was an unused substitute in Liverpool's Champions League Round of 16 second leg against Benfica.

After a successful season with the club, Anderson was named Swansea Young Player of the Year[8] scoring 10 goals in all competitions.

[10][11] After suffering with injury, Anderson eventually made his Forest debut against Queens Park Rangers on 18 October 2008.

On 23 January 2009, in an FA Cup fourth round qualifier, between Derby County and Nottingham Forest, Anderson suffered a serious injury in the second half of the game.

Anderson fell awkwardly after a challenge by Derby's Paul Connolly and suffered a broken arm and dislocated wrist.

However, due to Roberto Martínez leaving Swansea, personal terms were agreed and Forest signed the winger on a permanent basis for a fee of £250,000 on 30 June 2009.

Anderson's best moment in an Ipswich shirt came when he scored a crucial equaliser against bitter rivals Norwich City in the first leg of the semi-finals.

Anderson kindly offered to foot the bill for the damage caused, which was well received by the Town and many other football fans alike.

[34] After making 14 appearances, only being on the losing side once, Anderson's deal at Northampton was extended until the end of the 2019–20 season on 14 January 2020.