Bailey started to play rugby as a child at Dorchester RFC before joining the Bath academy at the age of fourteen.[2] In September 2020 he made his club debut for Bath in a league game against Worcester Warriors.[3]
In January 2022 Bailey received his first call-up to the senior England squad by coach Eddie Jones for the 2022 Six Nations Championship[5][6] however he subsequently withdrew due to suffering a hamstring injury during training.[7]
On the 19th of June 2022 Bailey made his senior England debut in a 52-21 defeat against the Barbarians at Twickenham, coming on for Bath teammate Joe Cokanasiga in the 66th minute.