The 1969 Boston Red Sox season was the 69th season in the franchise's Major League Baseball history. With the American League (AL) now split into two divisions, the Red Sox finished third in the newly established American League East with a record of 87 wins and 75 losses, 22 games behind the Baltimore Orioles, who went on to win the AL championship.

Richard Hirschfeld Williams was an American left fielder, third baseman, manager, coach and front-office consultant in Major League Baseball. Known especially as a hard-driving, sharp-tongued manager from 1967 to 1969 and from 1971 to 1988, he led teams to three American League pennants, one National League pennant, and two World Series triumphs. He is one of nine managers to win pennants in both major leagues, and joined Bill McKechnie in becoming only the second manager to lead three franchises to the Series. He and Lou Piniella are the only managers in history to lead four teams to seasons of 90 or more wins. Williams was inducted into the National Baseball Hall of Fame in 2008 following his election by the Veterans Committee.