Winchester came through the Linfield Academy, along with his twin brother, Jude, and made his first team debut for Linfield as a substitute on 1 May 2010 against Portadown.
Winchester came through the Linfield Academy. This was along with his twin brother. Winchester made his first team debut for Linfield as a substitute on 1 May 2010 against Portadown. Jude was his twin brother.