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- May 23 2023 2:30 PMBoys Varsity Baseball Canterbury vs. Salisbury School
- May 21 2023 11:00 AMBoys Varsity Baseball Canterbury vs. Williston Northampton
- May 20 2023 3:30 PMGirls Varsity Lacrosse Canterbury vs. Berkshire School
- May 20 2023 3:30 PMGirls Varsity Lacrosse Canterbury vs. Berkshire School
- May 20 2023 1:00 PMGirls Varsity Lacrosse Canterbury vs. Williston Northampton
- May 20 2023 1:00 PMGirls Varsity Lacrosse Canterbury vs. Pomfret
- May 17 2023 5:00 PMGirls JV Lacrosse Canterbury vs. Rumsey Hall
- May 17 2023 3:45 PMGirls Varsity Tennis Rye Country Day School vs. Canterbury
- May 17 2023 3:30 PMGirls Varsity Lacrosse Canterbury vs. Wilbraham & Monson Academy
- May 17 2023 3:00 PMBoys JV Baseball Canterbury vs. Suffield Academy
- May 17 2023 2:30 PMBoys Varsity Lacrosse Canterbury vs. Kent School
- May 16 2023 4:30 PMBoys Varsity Baseball Canterbury vs. Taft School
- May 13 2023 3:00 PMBoys Varsity Baseball Canterbury vs. Berkshire School
- May 13 2023 2:30 PMGirls Varsity Lacrosse Canterbury vs. Westminster School
- May 12 2023 4:30 PMBoys Varsity Lacrosse Canterbury vs. St. Luke's School
- May 11 2023 4:30 PMBoys Varsity Baseball Canterbury vs. Hamden Hall
- May 10 2023 4:30 PMGirls JV Lacrosse Canterbury vs. Litchfield
- May 10 2023 3:00 PMBoys JV Baseball Canterbury vs. Kingswood Oxford School
- May 10 2023 2:45 PMBoys JV Lacrosse Canterbury vs. Avon Old Farms
- May 9 2023 4:45 PMBoys JV Lacrosse Canterbury vs. Greenwich Country Day
- May 8 2023 4:30 PMGirls Varsity Lacrosse Canterbury vs. Greenwich Country Day
- May 8 2023 4:30 PMGirls Varsity Softball Canterbury vs. Kent School
- May 6 2023 2:00 PMGirls JV Lacrosse Canterbury vs. School of the Holy Child
- May 4 2023 4:45 PMBoys JV Lacrosse Canterbury vs. Hamden Hall
- May 3 2023 3:00 PMBoys Varsity Baseball Canterbury vs. Millbrook School
- May 1 2023 4:30 PMBoys JV Baseball Canterbury vs. Forman School
- May 1 2023 4:30 PMGirls Varsity Softball Canterbury vs. Westover
- Apr 29 2023 2:30 PMBoys JV Lacrosse Canterbury vs. The Frederick Gunn School
- Apr 26 2023 4:15 PMGirls Varsity Softball Canterbury vs. Hamden Hall
- Apr 26 2023 3:30 PMBoys Varsity Baseball Canterbury vs. Cheshire Academy
- Apr 26 2023 3:00 PMBoys JV Lacrosse Canterbury vs. Berkshire School
- Apr 24 2023 5:00 PMBoys Varsity Lacrosse Canterbury vs. Berkshire School
- Apr 24 2023 4:30 PMGirls Varsity Softball Canterbury vs. King School
- Apr 24 2023 4:15 PMBoys JV Baseball Canterbury vs. Rumsey Hall
- Apr 22 2023 4:00 PMBoys Varsity Lacrosse Canterbury vs. Millbrook School
- Apr 22 2023 3:30 PMBoys Varsity Baseball Canterbury vs. Williston Northampton
- Apr 22 2023 2:30 PMCo-Ed Varsity Track and Field Canterbury vs. Cheshire Academy
- Apr 21 2023 6:30 PMGirls Varsity Lacrosse Canterbury vs. The Hill Academy
- Apr 20 2023 4:35 PMBoys Varsity Baseball Canterbury vs. Salisbury School
- Apr 19 2023 4:15 PMGirls Varsity Softball Canterbury vs. Greenwich Country Day
- Apr 19 2023 2:30 PMGirls JV Lacrosse Canterbury vs. Berkshire School
- Apr 19 2023 2:30 PMGirls Varsity Lacrosse Canterbury vs. Berkshire School
- Apr 15 2023 4:30 PMGirls JV Lacrosse Canterbury vs. Kent School
- Apr 15 2023 2:30 PMBoys Varsity Baseball Canterbury vs. Salisbury School
- Apr 15 2023 2:30 PMGirls Varsity Lacrosse Canterbury vs. Kent School
- Apr 12 2023 3:00 PMBoys Varsity Baseball Canterbury vs. The Frederick Gunn School
- Apr 12 2023 2:30 PMGirls Varsity Softball Canterbury vs. Taft School
- Apr 8 2023 2:00 PMGirls Varsity Lacrosse Canterbury vs. The Frederick Gunn School
- Apr 8 2023 1:30 PMBoys JV Baseball Canterbury vs. The Frederick Gunn School
- Apr 8 2023 1:30 PMBoys Varsity Lacrosse Canterbury vs. Pomfret
- Apr 5 2023 3:30 PMBoys Varsity Baseball Canterbury vs. Pomfret
- Apr 5 2023 3:00 PMBoys Varsity Lacrosse Canterbury vs. Salisbury School
- Apr 5 2023 3:00 PMBoys JV Lacrosse Canterbury vs. Cheshire Academy
- Apr 1 2023 2:00 PMGirls Varsity Lacrosse Canterbury vs. The Hill School
- Mar 29 2023 2:45 PMGirls Varsity Lacrosse Canterbury vs. Berkshire School
- Mar 29 2023 2:30 PMGirls Varsity Lacrosse Canterbury vs. Millbrook School
- Feb 25 2023 4:00 PMBoys Varsity Basketball Canterbury vs. Avon Old Farms
- Feb 25 2023 2:30 PMBoys JV Basketball Canterbury vs. Avon Old Farms
- Feb 22 2023 3:45 PMBoys Varsity Ice Hockey Canterbury vs. Avon Old Farms
- Feb 22 2023 2:00 PMBoys JV Ice Hockey Canterbury vs. Kent School
- Feb 20 2023 5:30 PMGirls Varsity Ice Hockey Canterbury vs. Hotchkiss
- Feb 20 2023 4:15 PMBoys 3rds Basketball Canterbury vs. Rumsey Hall
- Feb 18 2023 7:00 PMBoys Varsity Ice Hockey Canterbury vs. Kent School
- Feb 18 2023 2:00 PMGirls JV Basketball Canterbury vs. Westover
- Feb 18 2023 2:00 PMGirls JV Ice Hockey Canterbury vs. Millbrook School
- Feb 17 2023 5:30 PMGirls Varsity Basketball Canterbury vs. School of the Holy Child
- Feb 15 2023 4:30 PMBoys Varsity Ice Hockey Canterbury vs. Williston Northampton
- Feb 15 2023 4:00 PMBoys Varsity Basketball Canterbury vs. Trinity-Pawling
- Feb 15 2023 4:00 PMBoys JV Ice Hockey Brunswick School vs. Canterbury
- Feb 15 2023 2:30 PMBoys JV Basketball Canterbury vs. Trinity-Pawling
- Feb 15 2023 2:25 PMGirls Varsity Ice Hockey Canterbury vs. Millbrook School
- Feb 15 2023 2:00 PMBoys 3rds Basketball Canterbury vs. The Frederick Gunn School
- Feb 11 2023 3:30 PMBoys Varsity Swimming Canterbury vs. Wilbraham & Monson Academy
- Feb 11 2023 3:00 PMBoys Varsity Ice Hockey Canterbury vs. Cushing Academy
- Feb 11 2023 2:30 PMBoys JV Basketball Canterbury vs. Berkshire School
- Feb 10 2023 7:00 PMGirls JV Ice Hockey Canterbury vs. Brewster Bulldogs
- Feb 10 2023 5:00 PMBoys JV Basketball Canterbury vs. The Frederick Gunn School
- Feb 10 2023 5:00 PMBoys Varsity Basketball Canterbury vs. The Frederick Gunn School
- Feb 8 2023 4:00 PMBoys Varsity Basketball Canterbury vs. Marianapolis
- Feb 8 2023 3:30 PMGirls Varsity Swimming Canterbury vs. Miss Porter's
- Feb 8 2023 2:30 PMGirls JV Basketball Canterbury vs. Hotchkiss
- Feb 8 2023 2:30 PMBoys JV Ice Hockey Canterbury vs. Trinity-Pawling