He played CIS football at St. Francis Xavier University and attended Our Lady of Mount Carmel Secondary School in Mississauga, Ontario.

[3] In his rookie season with the Eskimos, Bailey recorded 17 catches for a total of 219 yards.

[4] Bailey recorded his first CFL touchdown on August 21, 2015 against the Hamilton Tiger Cats.

On April 20, 2017, the Montreal Alouettes signed Bailey to a one-year contract worth an estimated $84,000.

[8] On February 19, 2020, it was announced that Bailey had signed with the BC Lions to a one-year contract.