1925
September 13 - The new Radio Station WDAD opened in Nashville. DeFord began playing on the station soon afterwards. He also played for WTNT subsequently.
October 5 - Radio Station WSM went on the air.
December 6 - Article appeared in the Nashville Tennessean about a French harp contest on radio station WDAD where DeFord Bailey "a negro boy" played "It Ain't Gonna Rain No Mo."
1926
June 19 - DeFord's first documented appearance on WSM in the newspaper radio schedule.
1927
April 1 - DeFord went to Atlanta to record with Columbia.
April 15 - DeFord went to New York City to record for Brunswick. His recordings were made in the McAlpin Hotel at 33rd and Broadway.
August - First of DeFord's records was issued. This was Brunswick 148 with "Evening Prayer Blues" and "Alcoholic Blues."
WSM became a station affiliate of the recently established National Broadcasting Company (NBC) radio network. WSM's association allowed it to receive broadcasts from Chicago, including the Music Appreciation Hour where Dr. Walter Damrosch was the master of ceremonies.
November - Brunswick released "Pan American Blues" and "Dixie Flyer Blues" on Brunswick 146.
December - Naming of the Opry by Judge Hay occurred one Saturday night this month. DeFord's music clearly inspired the naming and he was then the first performer on the newly named show. This occurred when Dr Damrosch had concluded his symphonic music program on the Music Appreciation Hour with a rendition of the on-rush of a locomotive. Judge Hay then told the Barn Dance audience that they had been listening to "Grand Opera" and would now listen to "Grand Ole Opry." At this point he introduced DeFord to play his realistic rendition of a train, the "Pan American Blues."
1928
October 2 - DeFord was recorded by Victor in the first recording session that took place in Nashville. He told Morton that he was the first one recorded, but the recording files indicate that he was third.
November 17 - W C Taylor, manager of the Pay Cash Grocery Co, came to Nashville to the Vandy-UT football game and was able to talk DeFord into going back with him to Knoxville to play on Radio Station WNOX. He played there at the St James Hotel for about three months before coming back to Nashville, and resuming his regular Saturday night performances. While he was in Knoxville he lived with a black couple.
November 27 - Knoxville News Sentinel reported that the Pay Cash Warblers and DeFord Bailey were performing at 8:00 PM on WNOX Radio.
Clark Odum, DeFord's foster father died in Detroit where he was working for Pontiac. His body was returned to Tennessee for burial and DeFord Bailey came back from Knoxville for the funeral.
1929
February 23 - Nashville Tennessean has DeFord Bailey listed on the program to play on the Opry that Saturday night, the first time he was listed since the December 1st appearance. He had moved back to Nashville sometime prior to this date.
DeFord married Ida Lee Jones. She was a young relative of his landlords, Mr. and Mrs. Will Sarden. They lived at 1306 Tremont.
1932
January 3 - DeFord Bailey, Jr. was born to DeFord and Ida Lee Bailey when they were living at 1314-13th Avenue, South in Nashville. They later moved to a large house at 130 LaFayette.
The tower of WSM was built right by the L & N main line going south at Brentwood,
1933
WSM organized their Artists Service Bureau, a booking agency designed to promote personal appearances for the WSM stars.
The Delmore Brothers came to the Opry.
DeFord set up his first shoeshine business in a barbershop operated by one of his uncles, George Reedy.
1934
October 15 - Dezoral Lee Bailey was born to DeFord and Ida Lee Bailey.
1936
December 29 - Christine Lamb Bailey was born to DeFord and Ida Lee Bailey. She was named about Christine Lamb, a white self-styled "blues singer" who was a regular on WSM's pop music shows.
1938
Roy Acuff and his Smokey Mountain Boys came to the Opry. In order to help publicize his group and draw a good crowd, he asked DeFord to accompany them on tours off and on during his first two or three years on the show.
1939
July - The Grand Ole Opry moved to the War Memorial Auditorium.
October - Bill Monroe came to the Opry and also quickly enlisted 'the Harmonica Wizard" to travel with him.
WSM publicity releases claimed that DeFord Bailey had never missed a broadcast.
1941
January 1 - Boycott began by WSM and other BMI radio stations of ASCAP tunes.
May 24 - Last time DeFord's name appeared in the radio listings in Nashville newspapers.