After several no playing time for the England player he was forced to request for a transfer due to his lack of game, he is a young player with the zeal of playing in the Chelsea team but there was an issue in selections for former coach Frank Lampard which couldn't favour him. Tomori was one of the player promoted from the youth team during the Chelsea transfer ban. When he request to move out of Chelsea to have a playing time no team were able to propose a permanent deal to sign him but Ac Milan came up with a loan deal with an option to buy if they are impressed in his performance.

Upon moving to AC Milan in the winter transfer he had his place in the first team and his performance was impressive for Ac Milan to propose a permanent transfer deal according to conditions of the loan in January. however, Ac Milan have now confirmed the signing of Chelsea player Fikayo Tomori. The 23-year-old defender has been able to convinced them and they have chosen to make the stay permanent.

Tomori quickly adapt to the team playing style and played 22 games for the club and he scored a single goal. The Englishman has been given a contract that will keep him at the club until June 30, 2025. This was a happy deal for Tomori has his dream has come true of making a regular position, his transfer fee is estimated to be £25 Million which will keep him till 2025.