| Day | Date | Opponent | Time |
| Saturday | 12/14 | @Marvelwood - 2nd Annual Skiff Mountain Scuffle | 7:30 AM |
| Wednesday | 1/8 | @Avon Old Farms (CT) | 2:30 PM |
| Saturday | 1/11 | @Loomis Chaffe (CT) JV Jamboree | 2:00 PM |
| Wednesday | 1/15 | @Woodstock (HVAL) | 1:00 PM |
| Saturday | 1/18 | @Loomis Chaffe (CT) JV Jamboree | 2:00 PM |
| Saturday | 1/18 | @Brunswick | TBD |
| Monday | 1/20 | @Salisbury | TBD |
| Wednesday | 1/22 | @Hackley School | TBD |
| Saturday | 1/25 | @Avon Old Farms (CT) JV Jamboree | 2:30 PM |
| Wednesday | 1/29 | @Marvelwood (HVAL) | 2:30 PM |
| Sunday | 2/1 | Northern New England Championships @Thayer Academy | 9:00 AM |
| Wednesday | 2/5 | @Loomis Chaffe (CT) JV Jamboree | 2:30 PM |
| Saturday | 2/8 | Western New England Championships @Brunswick | TBD |
| Friday | 2/14 | @New England Prep Championships | 5:00 PM |
| Saturday | 2/15 | @New England Prep Championships | 9:00 AM |
| Wednesday | 2/19 | @Storm King (HVAL) | 2:30 PM |
| Friday | 2/21 | Prep National Championships @Lehigh University | 9:00 AM |
| Tuesday | 2/25 | @Forman School (CT) | TBD |
