 Following his career-ending injury, Bailey asked the NHL if he could work as a linesman, but he was turned down.He coached the University of Toronto Varsity Blues men's ice hockey team hockey team from 1935 to 1940 and again after World War II from 1945 to 1949, winning three Canadian Interuniversity Athletics Union championships.He also worked as a timekeeper at Maple Leaf Gardens from 1938 to 1984, when the 81-year-old Bailey was told by Gardens owner Harold Ballard that his services were no longer needed.