Littlefield was head football coach at Greenville High School in Greenville for four years, and then in 1920 returned to the University of Texas as head track coach, freshman football coach, freshman basketball coach, and instructor in physical training.
Littlefield's tenure as head football coach at Greenville High School was followed by his return to the University of Texas in 1920, where he assumed various coaching and instructional positions, including track, football, basketball, and physical training.