Littlefield had quite an illustrious athletic career at UT.  He was on eight undefeated sports teams including football (1), track (4), and basketball (3).  He won 12 letters while at UT, only missing out on baseball because he did not have enough time to commit to the sport.  Although he did not earn a letter in baseball, he did pitch two varsity games.  He batted 1,000 during his time on the team.  He equaled the collegiate world record in the high hurdles 1914 and was never beaten. He was only beaten once in low hurdles.  In 1915, he was the Southwest Conference (SWC) scoring champion in basketball as well as an All American.  He was also an All SWC halfback in football.  While on the football team, he played multiple positions including, but not limited to, halfback and quarterback.  Not only was he on three athletic teams, but he was also a part of the Kappa Alpha Order and Sigma Delta Psi athletic fraternity.