According to the 2015-16 Official Norwich City Club Handbook, Tai Fleming was a member of Norwich City's Under-14s. He left Norwich at the age of 16, having joined aged 10..

On 2nd July 2018 he joined Yeovil Town as a scholar and became captain. He plays as a defender. On 12th September 2019 he was loaned to Melksham Town to gain first team experience alongside teammate Daniel Ojo.

On 21st July 2020, he returned to Norfolk, having been raised in Downham Market, and signed for Kings Lynn. "I am really excited to be joining what is my local club and cannot wait to get started,” said Fleming. “I enjoyed my time at Yeovil greatly and learned a lot but the chance to come home and play locally was far too good to turn down. The manager has an excellent squad here and I will be working very, very hard to break into the team and give 110pc every time I pull on a King’s Lynn shirt. My main position is as a defender but I can play midfield as well. I like to think I’m a bit of a terrier on the pitch, not letting people settle into their game or to dictate their style onto me. It’s a bit of a surreal feeling being here really but it’s a great opportunity for me and one which I aim to grab with both hands.”

He was loaned to Leiston in August 2021 and then later to Lowestoft..Lowestoft were relegated from the Southern League Premier Central division in late April 2022. He played 16 times for Lynn the following season when they finished runners-up in National League North.

On 23rd June 2023 Tai signed for Banbury United, re-uniting with Banbury manager Mark Jones who was his coach at Yeovil.