[1][2] In Bailey's first season as head baseball coach in 1927, the Cougar nine finished first in the Pacific Coast Conference North Division and won the PCC Tournament.
[1][5][6] Bailey's Cougar baseball teams won 14 conference titles (twelve PCC North Division and two AAWU), and went to the College World Series in 1950 and 1956.
The Cougars also made the NCAA tournament in his final two seasons of 1960 and 1961; he retired at age 65.
During his first stint with the Cougars before the war, Bailey had a friendly rivalry with Tubby Graves (1886–1960) of rival Washington;[13] Nine years older, Graves was one of his coaches at Texas A&M; he stepped down as head coach of the Huskies in 1946 and continued in the UW athletic department as a special assistant until his death.
Three years after his retirement, Bailey and his wife Frances were killed in an automobile collision in New Mexico in October 1964.