Before its New England Team Racing Championship win, the sailing team won second in the New England Fleet Race Championship, leading to qualification for the national Fleet Race Championship. The team placed fourth out of 20 teams at the Baker Team Race National Championship in Seabrook, TX, and eighth of 20 teams at the Mallory Fleet Race National Championship in San Diego, CA, both competitions organized by the Interscholastic Sailing Association. 

Complete season highlights:

• Varsity finished 11-3 in team racing
• Won Connecticut State Fleet Racing Championship 
• Received 2nd place at the New England Fleet Race Championship (the "O'Day"). We went on to place 8th in the National Fleet Race Championship (the Mallory) on June 4-5. 
• Won the New England Team Race Championship (The Presidents' Trophy), entering the competition ranked first in team racing on the season. That win qualified the team to compete in the National Team Racing Championship (the Baker), placing 4th.
• Team member Chapman Petersen ’22 won New England Singlehanded Championship in the fall, and Cal Kinnear ’25 represented Hotchkiss at the National Singlehanded Championship in December, finishing 16th.