Woodruff resigned a second time on January 6, 1950 to become the head football coach and athletic director at the University of Florida. Florida Gators head coach After the 1949 season, Woodruff replaced Raymond Wolf as the head football coach at the University of Florida in Gainesville, Florida. In order to induce Woodruff to coach the Florida Gators football team, the Florida Board of Control offered him a seven-year guaranteed contract at $17,000 per year. Woodruff's annual salary was $5,000 more than that of University of Florida President J. Hillis Miller. He was only 34 years old. Woodruff's coaching philosophy reflected that of his mentor, Tennessee Volunteers coach Robert Neyland, who emphasized defense and the kicking game. Ironically, his first Gators team in 1950 had a stellar offense and a weak defensive squad. The Gators offense was led by quarterback Haywood Sullivan, the first sophomore in Southeastern Conference (SEC) history to throw for more than 1,000 yards in a season, under Woodruff's offensive coordinator, Frank Broyles. Florida managed to upset the thirteenth-ranked Vanderbilt Commodores in Nashville, Tennessee, propelling the Gators into the top twenty teams of the Associated Press (AP) Poll for the first time. With the addition of Rick Casares to the backfield, Woodruff's 1951 Gators scored a 30–21 upset of the heavily favored Alabama Crimson Tide in their homecoming game in Tuscaloosa, Alabama. The 1952 Gators were Woodruff's most successful team, and the 1952 season included some of his most inspired coaching. After quarterback Haywood Sullivan left school early to accept a professional baseball contract with Boston Red Sox, Woodruff experimented with fullback Rick Casares at quarterback, but after three games it was apparent that Casares was not the solution. Woodruff's unconventional replacement, defensive back Doug Dickey, turned out to be exactly what the Gators needed at quarterback—a talented athlete and savvy game manager. Woodruff led his 1952 Gators team to the program's first top-twenty finish in the AP Poll, their first NCAA-sanctioned bowl game, the Gator Bowl, and a 14–13 bowl win over the Tulsa Golden Hurricane. At the conclusion of the 1952 season, senior defensive tackle Charlie LaPradd became the Gators' third first-team All-American. Although Woodruff was a talented administrator, he sometimes had difficulty expressing himself verbally. He would often stop mid-sentence to collect his thoughts, which Charlie LaPradd once described as "With [Woodruff's] long periods of silence, he would make you wonder if he was