In 1909, Dobson moved to Georgia Tech's arch-rival, Georgia. There, the new head coach, James Coulter, had no prior coaching experience. Dobson was hired as a co-coach and added new trick plays in an attempt to energize the offense. Still the team finished with a record of 2–4–2.
Dobson then moved to the University of Richmond, where he was athletic director and football, baseball, and basketball coach from 1913 to 1933, with one exception: in the abbreviated postwar season of 1918, rather than coaching the Richmond football team, he took over the South Carolina Gamecocks and led them to a record of 2–1–1. Dobson's overall football record at Richmond was 79–78–18, his baseball record was 153–112, and his basketball record was 153–106. Dobson was posthumously elected to the University of Richmond Athletic Hall of Fame in 1978.
In 1935, Dobson became an assistant at Maryland under head coach Jack Faber. The following season, he was promoted to head coach and served in that position through 1939. Dobson amassed an 18–21 record at Maryland.
Dobson finished his career as the 11th head football coach at The Apprentice School in Newport News, Virginia and he held that position for nine seasons, from 1940 until 1948. His coaching record at Apprentice was 25–26–2. A highlight at Apprentice was a 7–6 upset of the Virginia in 1943.