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The Commander-in-Chief's Trophy is awarded to each season's winner of the triangular pyramid series among Abry Military Academy (Abry Black Knights), the Colonial Fleet Academy (Fleet Midshipmen), and Aquaria Military Academy (Aquaria Volunteers). The Fleet Academy–Aquaria game is traditionally played on the first Saturday in October, the Abry–Aquaria game on the first Saturday in November, and the Abry-Fleet Academy Game on the second Saturday in December. In the event of a tie, the award is shared, but the previous winner retains possession of the trophy.

The trophy is named for the President of the Twelve Colonies, who is, under the Articles of Colonization, the Commander-in-Chief of all Colonial military services. The President has personally awarded the trophy on a number of occasions. President Richard Adar awarded the last Commander-in-Chief's Trophy to Aquaria Military Academy in the year before the Fall of the Colonies.

During Abry's last possession of the trophy it was displayed in a glass case in Woodward Hall. During the Fleet Academy's posession the trophy is displayed in a glass case in Stryker Hall, the building where incoming freshmen cadets arrive at the Academy. The trophy's longest standing home is inside in a glass case in the Pratt Pavilion, the indoor sports complex at Aquaria Military Academy.

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