Career
Football
Middlekauff was a prominent fullback for coach James Van Fleet and coach Tom Sebring"s Florida Gators football team of the from 1923 to 1924, and 1926 to 1927. One accounts recalls he "rams a line and can back one up to perfection." Jeff Moshier called him Florida"s greatest fullback. In 1927, the Florida Alumnus, the official organ of the Florida Alumni, agreed.
= 1924 In the 14–7 loss to Army, Middlekauff broke his left leg on what coach Van Fleet argued was an uncalled clipping penalty.
Middlekauff had only just returned to the team = 1926 Middlekauff returned in 1926.
= 1927 He was captain of the team in 1927, elected after the regular captain Frank Oosterhoudt was declared ineligible. The season started poorly including an 0–12 upset to Davidson before Middlekauff was elected captain, and was much better afterwards.
He was the only player of the Gators selected All-Southern that year.
In an all-star game of Pacific Coast stars against Southern stars hampered by rain, Middlekauff got the only score of the game in an 8–0 victory for the South. After practicing law in Miami for a short time, Middlekauff was a professional boxer, scoring several knockouts. In a professional boxing career as a heavyweight, he had record of 6 Wins (5 by knockout) 7 Losses (5 by knockout) and 1 Draw in 14 bouts.
Middlekauff also wrestled professionally from 1930 to 1946.
He once met former Georgia Technical fullback Doug Wycoff in a match, the main event at the Atlanta Municipal Auditorium for Georgia Championship promoter Henry Weber. One account reads "Bill has a habit of hurling his 235 pounds of brawn at his rival to bring him down almost exactly as he did in blocking a would-be tackler out of the play during his football days.".