| Upcoming Events | Date & Time |
| Meeting for all modified sports teams: coaches and student-athletes after school until 3:45 PM | Tue 11/17/2026 3:00 pm - 4:00 pm |
| (bus at 2:45 PM) ⭐🟩🚍🤼♂️AWAY VARSITY WRESTLING PAWLING @ Chester HS | Thu 12/03/2026 5:00 pm - 6:30 pm |
| ⭐🟩🚍🤼♂️AWAY VARSITY WRESTLING PAWLING @ PATRIOT INVITATIONAL - JJEF (bus at 6:45 am) | Sat 12/12/2026 9:00 am - 5:00 pm |
| ⭐⭐⭐⭐⭐🟥🤼♂️HOME VARSITY WRESTLING "ROUND ROBIN TOURNAMENT" (doors open 7:15 am) | Sat 12/19/2026 9:00 am - TBD |
| ⭐🟩🚍🤼♂️AWAY SECTION 1 CHAMPIONSHIP TOURNAMENT ⭐⭐⭐⭐VARSITY WRESTLING PAWLING @ Westchester County Center | Fri 02/05/2027 TBD |
| ⭐🟩🚍🤼♂️AWAY SECTION 1 CHAMPIONSHIP TOURNAMENT ⭐⭐⭐⭐VARSITY WRESTLING PAWLING @ Westchester County Center | Sat 02/06/2027 TBD |
| ⭐🟩🚍🤼♂️AWAY SECTION 1 CHAMPIONSHIP TOURNAMENT ⭐⭐⭐⭐VARSITY WRESTLING PAWLING @ Westchester County Center | Sun 02/07/2027 TBD |
| 🏒🏀🤼♂️⛷🤸🏼♂️🏃🏼♀️🏃🏼♂️🩰⭐⭐⭐⭐⭐⭐⭐ Pawling High School Winter Sports Awards⭐ | Thu 03/18/2027 6:30 pm - 9:30 pm |