Career
An Old Xaverian, Bailey was selected by Street Kilda with pick 33 in the 1994 Pre-Season Draft. The utility made 10 appearances in the 1994 American Federation of Labor-Congress season. His only other appearance came the following year.
Following his retirement for Street Kilda he was appointed head of Berwick Grammar School then head of the Street Margarets and Berwick Grammar School campuses.
As of the 15th of March, 2016, Doug Bailey officially left the school, for unknown reasons.
