Athletic teams from The Frederick Gunn School and Canterbury School come together in the spirit of competition, sportsmanship, and camaraderie to participate in Canterbury Day every November. The one-day event rotates between the two campuses on an annual basis.
The Gunn-Canterbury Cup is a year-long competition in which one point is awarded to the winner of each head-to-head interscholastic athletic contest, regardless of level, between Canterbury and FGS is worth one point. Ties are worth half a point. At the end of the year, the school with the most points wins the cup.
Canterbury currently holds the Gunn-Canterbury Cup, winning the 2021-2022 yearlong competition by the score 20-19.