 He then attended Peacock Military Academy in San Antonio and Marshall Training School, and from 1912 to 1916 was a student at the University of Texas, where he earned twelve letters, in football, basketball, and track.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.He remained there until 1961, winning 25 Southwest conference championships in track, and also serving as head football coach from 1927 to 1933, during which time the university won two Southwest Conference championships.