| Date | Time | Sport | Opponent | Location | More Info | Rescheduled? |
| Friday, Feb 10 | 4:30 | Boys' Varsity Basketball | Salisbury School | H | | |
| Friday, Feb 10 | 4:30 | Girls' Thirds Basketball | Choate Rosemary Hall | A | | |
| Friday, Feb 10 | 5:00 | Boys' Junior Varsity Basketball | Salisbury School | A | | |
| Saturday, Feb 11 | 2:00 | Girls' Varsity Squash | Deerfield Academy | H | | |
| Saturday, Feb 11 | 2:00 | Girls' Junior Varsity Squash | Deerfield Academy | H | | |
| Saturday, Feb 11 | 2:30 | Boys' Thirds Basketball | Westminster School | A | | |
| Saturday, Feb 11 | 2:30 | Girls' Varsity Basketball | Hotchkiss School | H | | |
| Saturday, Feb 11 | 2:30 | Girls' Varsity Hockey | Hotchkiss School | H | | |
| Saturday, Feb 11 | 2:30 | Girls' Junior Varsity Hockey | Hotchkiss School | A | | |
| Saturday, Feb 11 | 2:30 | Boys' Thirds Squash | Salisbury School | A | | |
| Saturday, Feb 11 | 3:30 | Boys' Varsity Squash | Deerfield Academy | A | | |
| Saturday, Feb 11 | 3:30 | Boys' Junior Varsity Squash | Deerfield Academy | A | | |
| Saturday, Feb 11 | 3:30 | Girls' Thirds Squash | Miss Porter's School | H | JV | |
| Saturday, Feb 11 | 4:00 | Girls' Junior Varsity Basketball | Hotchkiss School | H | | |
| Saturday, Feb 11 | 4:00 | Boys' Thirds Hockey | Avon Old Farms School | A | | |
| Saturday, Feb 11 | 4:15 | Boys' Varsity Hockey | Hotchkiss School | H | | |
| Saturday, Feb 11 | 4:15 | Boys' Junior Varsity Hockey | Gunnery School | H | | |
| Saturday, Feb 11 | 5:30 | Boys' Junior Varsity Basketball | Avon Old Farms School | H | | |
| Saturday, Feb 11 | 7:00 | Boys' Varsity Basketball | Avon Old Farms School | H | | |
| Saturday, Feb 11 | 9:00 | Varsity Wrestling | WNEPSAC | A | @Hotchkiss | |
| Monday, Feb 13 | 4:30 | Boys' Junior Varsity Basketball | Greenwich Country Day | H | | |
| Monday, Feb 13 | 4:30 | Girls' Thirds Basketball | Millbrook School | A | | |
| Wednesday, Feb 15 | | Competitive Skiing | NEPSAC | A | | |
| Wednesday, Feb 15 | 2:30 | Boys' Varsity Basketball | Kent School | H | | |
| Wednesday, Feb 15 | 2:30 | Boys' Junior Varsity Basketball | Kent School | H | | |
| Wednesday, Feb 15 | 2:30 | Boys' Thirds Basketball | Kent School | A | | |
| Wednesday, Feb 15 | 2:30 | Boys' Junior Varsity Hockey | Avon Old Farms School | A | | |
| Wednesday, Feb 15 | 2:30 | Girls' Varsity Hockey | Westminster School | A | | |
| Wednesday, Feb 15 | 2:30 | Girls' Thirds Squash | Millbrook School | H | | |
| Wednesday, Feb 15 | 4:00 | Girls' Varsity Basketball | Williston Northampton School | H | | |
| Wednesday, Feb 15 | 4:00 | Girls' Junior Varsity Basketball | Williston Northampton School | H | | |
| Wednesday, Feb 15 | 4:00 | Boys' Varsity Hockey | Deerfield Academy | H | | |
| Wednesday, Feb 15 | 4:00 | Girls' Junior Varsity Hockey | Westminster School | A | | |
| Wednesday, Feb 15 | 4:15 | Boys' Thirds Hockey | Hotchkiss School | A | JV | |
| Friday, Feb 17 | | Varsity Wrestling | New England Tournament | A | @NMH | |
| Friday, Feb 17 | 4:15 | Competitive Skiing | BSL Slalom | A | - JV@Sundown | |
| Saturday, Feb 18 | | Varsity Wrestling | New England Tournament | A | @NMH | |
| Saturday, Feb 18 | 2:00 | Boys' Varsity Hockey | Choate Rosemary Hall | H | | |
| Saturday, Feb 18 | 2:00 | Boys' Thirds Hockey | Kent School | A | | |
| Saturday, Feb 18 | 2:00 | Girls' Junior Varsity Hockey | Choate Rosemary Hall | A | | |
| Saturday, Feb 18 | 2:30 | Boys' Junior Varsity Basketball | Loomis Chaffee School | H | | |
| Saturday, Feb 18 | 2:30 | Boys' Thirds Basketball | Berkshire School | H | | |
| Saturday, Feb 18 | 2:30 | Girls' Varsity Basketball | Choate Rosemary Hall | A | | |
| Saturday, Feb 18 | 2:30 | Boys' Junior Varsity Squash | Hotchkiss School | A | | |
| Saturday, Feb 18 | 2:30 | Girls' Varsity Squash | Hotchkiss School | H | | |
| Saturday, Feb 18 | 2:30 | Girls' Junior Varsity Squash | Hotchkiss School | H | | |
| Saturday, Feb 18 | 3:30 | Boys' Varsity Squash | Hotchkiss School | A | | |
| Saturday, Feb 18 | 4:00 | Boys' Varsity Basketball | Loomis Chaffee School | H | | |
| Saturday, Feb 18 | 4:00 | Girls' Junior Varsity Basketball | Choate Rosemary Hall | A | | |
| Saturday, Feb 18 | 4:00 | Boys' Junior Varsity Hockey | Choate Rosemary Hall | A | | |
| Saturday, Feb 18 | 4:00 | Girls' Varsity Hockey | Choate Rosemary Hall | H | | |
| Tuesday, Feb 21 | 4:30 | Girls' Varsity Basketball | Miss Porter's School | H | | |
| Wednesday, Feb 22 | 2:00 | Boys' Junior Varsity Hockey | Trinity-Pawling School | H | | |
| Wednesday, Feb 22 | 2:00 | Boys' Thirds Hockey | Trinity-Pawling School | H | | |
| Wednesday, Feb 22 | 2:00 | Competitive Skiing | BSL SL Championships | A | @Sundown | |
| Wednesday, Feb 22 | 2:30 | Boys' Junior Varsity Basketball | Avon Old Farms School | A | | |
| Wednesday, Feb 22 | 2:30 | Boys' Thirds Basketball | Avon Old Farms School | H | | |
| Wednesday, Feb 22 | 2:30 | Girls' Varsity Basketball | Berkshire School | H | | |
| Wednesday, Feb 22 | 2:30 | Girls' Junior Varsity Hockey | Loomis Chaffee School | A | | |
| Wednesday, Feb 22 | 2:30 | Boys' Varsity Squash | Westminster School | H | | |
| Wednesday, Feb 22 | 2:30 | Boys' Junior Varsity Squash | Westminster School | H | | |
| Wednesday, Feb 22 | 2:30 | Girls' Varsity Squash | Westminster School | A | | |
| Wednesday, Feb 22 | 2:30 | Girls' Junior Varsity Squash | Westminster School | A | | |
| Wednesday, Feb 22 | 2:45 | Boys' Varsity Hockey | Trinity-Pawling School | A | | |
| Wednesday, Feb 22 | 4:00 | Boys' Varsity Basketball | Avon Old Farms School | A | | |
| Wednesday, Feb 22 | 4:00 | Girls' Junior Varsity Basketball | Berkshire School | H | | |
| Wednesday, Feb 22 | 4:00 | Girls' Varsity Hockey | Berkshire School | H | | |
| Wednesday, Feb 22 | 4:00 | Boys' Thirds Squash | Westminster School | H | | |
| Wednesday, Feb 22 | 4:00 | Girls' Thirds Squash | Westminster School | A | | |
| Friday, Feb 24 | 3:30 | Girls' Thirds Basketball | Indian Mountain School | H | | |
| Saturday, Feb 25 | | Boys' Varsity Squash | NEPSA | A | @Exeter | |
| Saturday, Feb 25 | | Girls' Varsity Squash | New England Tournament | A | | |
| Saturday, Feb 25 | | Varsity Wrestling | New England Tournament | | JV | |
| Saturday, Feb 25 | 2:30 | Boys' Junior Varsity Basketball | Westminster School | A | | |
| Saturday, Feb 25 | 2:30 | Boys' Thirds Basketball | Suffield Academy | A | | |
| Saturday, Feb 25 | 2:30 | Boys' Varsity Hockey | Hotchkiss School | A | | |
| Saturday, Feb 25 | 2:30 | Boys' Thirds Hockey | Westminster School | H | | |
| Saturday, Feb 25 | 2:30 | Girls' Junior Varsity Hockey | Hotchkiss School | H | | |
| Saturday, Feb 25 | 2:30 | Varsity Wrestling | New England Tournament | H | JV Tournament | |
| Saturday, Feb 25 | 3:00 | Girls' Varsity Basketball | Hotchkiss School | A | | |
| Saturday, Feb 25 | 3:00 | Girls' Junior Varsity Basketball | Hotchkiss School | A | | |
| Saturday, Feb 25 | 4:00 | Boys' Varsity Basketball | Westminster School | A | | |
| Saturday, Feb 25 | 4:00 | Boys' Junior Varsity Hockey | Hotchkiss School | H | | |
| Saturday, Feb 25 | 4:30 | Girls' Varsity Hockey | Hotchkiss School | A | | |
| Sunday, Feb 26 | | Boys' Varsity Squash | NEPSA | A | @Exeter | |