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- May 21 2022 11:00 AMBoys Varsity Baseball Canterbury vs. Cheshire Academy
- May 21 2022 11:00 AMGirls Varsity Lacrosse Canterbury vs. Williston Northampton
- May 18 2022 3:00 PMBoys Varsity Baseball Canterbury vs. Suffield Academy
- May 18 2022 2:30 PMGirls Varsity Softball Canterbury vs. Millbrook School
- May 17 2022 4:30 PMGirls Varsity Softball Canterbury vs. Hopkins School
- May 14 2022 3:00 PMBoys JV Baseball Canterbury vs. Berkshire School
- May 14 2022 2:30 PMGirls JV Lacrosse Canterbury vs. Suffield Academy
- May 14 2022 2:00 PMBoys Varsity Lacrosse Canterbury vs. Portsmouth Abbey School
- May 13 2022 4:15 PMBoys Varsity Baseball Canterbury vs. Hamden Hall
- May 11 2022 4:30 PMGirls Varsity Lacrosse Canterbury vs. School of the Holy Child
- May 11 2022 3:30 PMGirls Varsity Softball Canterbury vs. The Frederick Gunn School
- May 11 2022 3:00 PMBoys JV Lacrosse Canterbury vs. Greenwich Country Day
- May 11 2022 3:00 PMBoys Varsity Baseball Canterbury vs. Berkshire School
- May 9 2022 5:00 PMBoys Varsity Lacrosse Canterbury vs. Cheshire Academy
- May 9 2022 4:30 PMGirls Varsity Softball Canterbury vs. School of the Holy Child
- May 9 2022 4:30 PMBoys JV Baseball Canterbury vs. Trinity-Pawling
- May 7 2022 6:30 PMBoys Varsity Lacrosse Canterbury vs. Williston Northampton
- May 7 2022 2:30 PMBoys Varsity Baseball Canterbury vs. Millbrook School
- May 6 2022 4:30 PMBoys JV Lacrosse Canterbury vs. The Frederick Gunn School
- May 4 2022 3:30 PMGirls JV Lacrosse Canterbury vs. Hopkins School
- May 4 2022 3:30 PMGirls Varsity Lacrosse Canterbury vs. Hopkins School
- Apr 30 2022 4:15 PMBoys Varsity Lacrosse Canterbury vs. The Frederick Gunn School
- Apr 30 2022 2:30 PMBoys Varsity Baseball Canterbury vs. Wilbraham & Monson Academy
- Apr 30 2022 1:30 PMGirls Varsity Lacrosse Canterbury vs. Cheshire Academy
- Apr 27 2022 5:00 PMBoys Varsity Lacrosse Canterbury vs. Albany Academy
- Apr 27 2022 3:00 PMBoys Varsity Baseball Canterbury vs. Cheshire Academy
- Apr 27 2022 2:30 PMGirls JV Lacrosse Canterbury vs. Millbrook School
- Apr 27 2022 2:30 PMGirls Varsity Lacrosse Canterbury vs. Millbrook School
- Apr 23 2022 2:30 PMGirls Varsity Softball Canterbury vs. Westminster School
- Apr 23 2022 2:10 PMGirls JV Lacrosse Canterbury vs. The Frederick Gunn School
- Apr 23 2022 2:00 PMBoys JV Baseball Canterbury vs. King School
- Apr 22 2022 4:30 PMBoys Varsity Baseball Canterbury vs. Trinity-Pawling
- Apr 20 2022 3:00 PMBoys Varsity Baseball Canterbury vs. Salisbury School
- Apr 19 2022 4:00 PMBoys JV Lacrosse Canterbury vs. Nonnewaug High School
- Apr 18 2022 4:30 PMBoys Varsity Baseball Canterbury vs. St. Luke's School
- Apr 16 2022 2:30 PMBoys JV Lacrosse Canterbury vs. Trinity-Pawling
- Apr 16 2022 2:30 PMBoys Varsity Lacrosse Canterbury vs. Greenwich Country Day
- Apr 13 2022 4:15 PMBoys JV Baseball Canterbury vs. Suffield Academy
- Apr 13 2022 3:00 PMBoys Varsity Lacrosse Canterbury vs. Suffield Academy
- Apr 13 2022 3:00 PMBoys JV Lacrosse Canterbury vs. Suffield Academy
- Apr 13 2022 1:45 PMBoys Varsity Baseball Canterbury vs. The Frederick Gunn School
- Apr 11 2022 4:30 PMBoys Varsity Baseball Canterbury vs. Greenwich Academy
- Apr 11 2022 4:30 PMBoys Varsity Lacrosse Canterbury vs. Hamden Hall
- Apr 9 2022 2:00 PMGirls JV Lacrosse Canterbury vs. Litchfield
- Apr 6 2022 2:30 PMGirls Varsity Lacrosse Canterbury vs. Taft School
- Apr 6 2022 2:30 PMGirls JV Lacrosse Canterbury vs. Taft School
- Apr 2 2022 7:00 PMGirls Varsity Lacrosse Canterbury vs. The Hill School
- Apr 2 2022 3:00 PMBoys Varsity Lacrosse Canterbury vs. King School
- Apr 2 2022 2:30 PMBoys Varsity Baseball Canterbury vs. Hotchkiss
- Mar 30 2022 5:00 PMBoys Varsity Lacrosse Canterbury vs. New Milford High School
- Mar 6 2022 2:15 PMBoys Varsity Basketball Canterbury vs. The Rivers School
- Mar 5 2022 2:45 PMBoys Varsity Basketball Canterbury vs. Millbrook School
- Mar 2 2022 4:00 PMBoys Varsity Basketball Canterbury vs. Kingswood Oxford School