Freeland was born on January 1, 1887 in Turnersville, Texas and died on August 15, 1953 in Brownwood, Texas. He played football and baseball at Vanderbilt University, from which he graduated in 1912. He was nominated though not selected for an Associated Press All-Time Southeast 1869-1919 era team. In 1915, Freeland coached football at TCU, compiling a 4–5 record. In 1922 and 1923, Freeland co-coached the SMU Mustangs football team with his former teammate at Vanderbilt, Ray Morrison. The two effectively shared the heading coaching duties, with Morrison focusing on the backfield and ends, and Freeland mentoring the linemen. In 1925, Freeland became the first coach of the Texas Tech Red Raiders football team, then known then as the Matadors. He coached football at Texas Tech from 1925 to 1928, where he had a 21–10–6 record. Freeland was also the first head coach of the Texas Tech Red Raiders baseball team and Texas Tech's first athletic director. He is credited with designing Texas Tech's Double T logo and had it put on the sweaters of football players.