In 1952 John Barnes and Allen Cole purchased Dumford Academy, located on Bartmer Avenue, and renamed it Whitfield School.

During spring break of 1957, Barnes and Cole and the school moved into a residential house in Creve Coeur, some of which had been converted into classrooms.

It also added an atrium, visible from nearby Ladue Road, as an entrance to the Cady Athletic Center and Woods Hall.

In 2022, work in the humanities wing turned an area informally known as Stonehenge into the Koman Commons, a large staircase designed for seating and out-of-classroom teaching nicknamed the Whit Pit.

Students in grades 6-12 take required courses each year in the following departments: English, social studies, science, mathematics, and language.

Notable rivalries for soccer are John Burroughs School, Westminster, Bayless, Springfield Catholic, and Pembroke Hill.

In 2011, the Whitfield hockey team won the Founder's Cup by beating Parkway South High School 7–5, and Nick Kunin was named the MVP of the game.

In 2012, the Warriors won their second Wickenheiser Cup Championship by defeating Lutheran High School South 6 to 5 in an exciting game that was tied through regulation and the 10-minute sudden death period.

MVP senior Hunt Lucas scored the only goal in the shoot out, and junior goalie Alan Eidelman stopped all three chances to secure the win.

This paper contained featured articles about large-scale issues that affect society, movies and other forms of entertainment, and school-wide news and polls.

The school's online magazine, The Aeneid, offered more time-sensitive articles and addressed more urgent issues than The Odyssey.

These anonymous submissions are reviewed by a selection committee which decides, based on several factors, what should be included in that year's edition.

Every year students adopt a family from the St. Patrick Center, a local charitable organization that supports the unhoused,[6] and help them have a special holiday season.