Keshi Anderson trialled for Norwich City's Under-21s in January 2015 playing in a 0-0 draw at Sunderland on 19th January 2015. He had scored 19 goals in 29 appearances this season for Southern League Division One Central side Barton Rovers. Luton were also interested in him.

19 year old Keshi then joined Brentford on trial, scoring a hat-trick after coming on as substitute in a friendly against Crystal Palace. This prompted Palace to sign him on 2nd February 2015 for £7,000 along with Wilfried Zaha from Manchester United and South Korean international Lee Chung-yong from Bolton. He scored on his debut for Palace's Under-21s coming on as substitute against Millwall.

On 24th September 2015, he was loaned to Doncaster Rovers on a 28 day loan deal. He made nine appearances, scoring three goals.

Anderson was loaned to Bolton Wanderers on 31st Auguist 2016. He made 10 appearances for Wanderers, scoring once (on his debut on 3rd September 2016 against Southend).

He was loaned again on 17th January 2017, joining Northampton Town until the end of the 2016/17 season.

He was loaned out for a fourth time on 31st August 2017 joining League Two side Swindon on a six month loan. This was turned into a permanent deal on 16th January 2018 with Anderson signing a two and a half year deal.

On 29th June 2020 Keshi joined Blackpool. He had played 20 league games for Swindon scoring six goals.

Anderson played as Blackpool lost 3-2 at home to Millwall on 28th April 2023 and were relegated to League One. On 16th May 2023 it was announced that Keshi would leave Blackpool on the expiry of his contract in June 2023.

After a successful trial, he signed a one year contract with Birmingham City on 22nd July 2023.