Spring 1950
Faculty member Robert Booker takes over as headmaster when Mr. Stapleton leaves.

1950–51
Country Day only fields two boys' teams, football and basketball, with no teams for girls. Boys' softball is added in 1952.

May 1951
Country Day announces plans to offer financial aid to at least 20% of its students.

1952–53
The school, which now goes through grade eight, fields its first girls' basketball team. There are now 126 students enrolled in preschool through eighth grade.

December 1955
The first Christmas Breakfast, now called the Holiday Breakfast, is held. The school hosts the event, and a full meal is served to the entire CCDS community.

June 1955
David Howe becomes headmaster, a post he will fill for 14 years.

1958–59
French is added to the CCDS curriculum from preschool through grade nine.

1958–59
The entire faculty consists of just 17 teachers and staff. Among Mr. Howe's accomplishments is building the faculty from 12 in 1955 to 52 in 1969 and increasing enrollment from 150 students in 1955 to 550 in 1969.

November 1959
After a gift of 30 acres of land on Carmel Road donated by Angelia and James J. Harris—and with $480,000 of a $700,000 capital fund drive already raised—the school's two governing boards approve the construction of a new campus to house the school. Construction begins immediately.