Born in Enfield, he began his career with Barnet, where he featured on the bench for the first team during the 2012–13 season.

Moved to Fulham for the 2014–15 season and was loaned out to Conference South side Farnborough for the second half of the season, making 14 appearances. Dillon briefly joined Bedford Town, before joining Colchester United on a one-year development contract in September 2015.

By the 2018-19 season he was a regular first team player, making 24 Football League appearances. After moving to Queens Park Rangers on a two-year deal, he had loan spells at Hibernian, Burton Albion, Yeovil Town and Aldershot Town, but didn’t make a first team appearance for his parent club.

He took a year out following his release in 2022 before joining Haringey Borough for the 2023-24 season, then Hamlet the following summer.

He has one full international cap for Jamaica, against Costa Rica in the CONCACAF Gold Cup of 2021.