In 1921 a silver spoon disappeared from Mrs. Batchelder’s silver tea service. It was believed by many that a Kent football player removed it during a post-game tea at the headmaster’s house. This social gathering followed a particularly intense Loomis-Kent gridiron match up. Loomis School historian, Lou Fowles later recalled in his book, The Harvest of Our Lives, “During the course of the ‘hard-fought’ encounter, Mr. Batchelder, apparently incensed by the rough playing of one of the Kent linemen, came running onto the field to protest. This procedure was not unique with Mr. Batchelder, for as Charlie Pratt, one of the players, later observed, “Mr. Batchelder was always running onto the field.’ But in this game, Father Sill who, in turn, had his ideas about who should be on the playing field also appeared. There were angry words…. The tea at the headmaster's house after the game provided the sequel that made the game an enduring legend.”

The two schools would not meet again on the football field until 1934.

In 1947, on the occasion of Mr. B’s 25th year as Loomis’ Headmaster, the spoon was returned to Windsor. Father Chalmers, Sills’ successor, presented this to Batchelder along with an enlarged replica to serve as a trophy for the victor of the annual meeting of the two teams. The scores of the each year’s game were engraved on the spoon. This Kent Day tradition continued for sixty-five years and will resume after a nine-year hiatus in November 2021.

In the 1980s, the two schools’ fall sports teams also began competing for The Bowl. This trophy goes to the school that wins the most games played between Kent and Loomis Chaffee on the annual Kent Day.