Hill hailed from Joaquin, Texas. His father, Garfield Hill, served as principal of Weldon High School in Gladewater, Texas. Winston was a tennis champion in high school. He played both offensive and defensive line in college at Texas Southern University and was an All-American.
Hill was drafted by the Baltimore Colts in 1963, but signed as a free agent with New York’s American Football League franchise in the same year that they became the New York Jets, and went on to record the tenth-longest string of starts in pro football history at 174. As left offensive tackle for the Jets, he spent his career protecting Joe Namath's blind side and opening holes for the likes of Emerson Boozer, Matt Snell and John Riggins. He was an American Football League All-Star in 1964, 1967, 1968 and 1969, and a Pro Bowl selection in 1970, 1971, 1972 and 1973. Despite these achievements, he has yet to be inducted into or even nominated for the Pro Football Hall of Fame. He and Joe Namath joined the Los Angeles Rams in 1977; Namath retired after one season and Hill after three games.
Hill was an overpowering blocker who was instrumental in opening gaping holes for Jet running backs during the 1968 season, in which they won the Eastern division title with 11 wins and 3 losses and gained as a team 1608 yards rushing and 3574 yards passing. Hill also starred in the Third Professional AFL-NFL World Championship Game (Super Bowl III), as the Jets decimated the right side of the Baltimore Colts' defensive line with Ordell Braase at end against Hill and Fred Miller at tackle against Bob Talamini, so that Matt Snell gained 121 yards rushing in the Jets' 16–7 upset victory.
In 1970 Hill was selected by a panel of members of the AFL's Hall of Fame Board of Selectors to the second-team All-time All-American Football League Team. He was a member of the New York Jets' All-Time Four Decade Team, which was determined by the fans in 2003. Hill was a 1986 inductee into the Texas Southern University Sports Hall of Fame.
The 2009 NFL season was the 50th season for the eight original AFL teams, and that anniversary was commemorated throughout the season with 16 "AFL Legacy Games." One of those games, pitting the NY Jets against the Miami Dolphins, took place in New York on Sunday November 1; designated by the NFL as "Winston Hill Day". Hill's daughter, opera singer Heather Hill, opened the game by singing the national anthem, and fifteen of Hill's former teammates and other ex-Jets joined the festivities. As part of the celebration, Hill's jersey, #75, was retired during the halftime ceremonies.
On Monday August 16, 2010, during halftime of the first game played at the New Meadowlands Stadium (a preseason opener; Jets vs. Giants), Hill was inducted into the Jets Ring of Honor. This selection was made by an internal committee led by Jets Chairman and CEO Woody Johnson.
The Professional Football Researchers Association named Hill to the PRFA Hall of Very Good Class of 2014
Hill brought a smoker and his cooking talents to Centennial, Colorado in the early 1990s and opened a small restaurant - Winston Hill's BBQ or Winston Hill's Ribs & Stuff. It was still active as of 2014.
Hill died on April 26, 2016 at the age of 74.