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League game
| Date/Time | Matchup | Status | Score | Venue |
|---|---|---|---|---|
| Sep 9, 2026, 5:15 PM | Pawling High School vs. Riverside High School | FINAL | 3 - 0 | Pawling High School |
| Sep 10, 2026, 4:30 PM | Pawling High School vs. Haldane Central High School District | FINAL | 1 - 3 | Haldane Central High School District |
| Sep 14, 2026, 6:45 PM | Pawling High School vs. Keio Academy of New York | FINAL | 1 - 3 | Pawling High School |
| Sep 15, 2026, 4:30 PM | Pawling High School vs. Greenburgh-North Castle | FINAL | 3 - 0 | Greenburgh-North Castle |
| Sep 17, 2026, 4:30 PM |
| Pawling High School vs. North Salem Middle/High School |
FINAL |
| 0 - 3 |
| North Salem Middle/High School |
| Sep 18, 2026, 4:45 PM | Pawling High School vs. Riverside High School | FINAL | 3 - 0 | Riverside High School |
| Sep 23, 2026, 4:30 PM | Pawling High School vs. Croton Harmon High School* | FINAL | 0 - 3 | Croton Harmon High School |
| Sep 25, 2026, 5:30 PM | Pawling High School vs. Westlake High School | FINAL | 0 - 3 | Westlake High School |
| Sep 29, 2026, 6:15 PM | Pawling High School vs. Hastings High School* | FINAL | 0 - 3 | Pawling High School |
| Oct 1, 2026, 4:30 PM | Pawling High School vs. Irvington High School* | FINAL | 0 - 3 | Irvington High School |
| Oct 2, 2026, 6:30 PM | Pawling High School vs. Keio Academy of New York | FINAL | 0 - 3 | Keio Academy of New York |
| Oct 5, 2026, 6:45 PM | Pawling High School vs. Putnam Valley High School* | FINAL | 0 - 3 | Pawling High School |
| Oct 6, 2026, 4:30 PM | Pawling High School vs. Dobbs Ferry High School* | FINAL | 0 - 3 | Dobbs Ferry High School |
| Oct 8, 2026, 4:30 PM | Pawling High School vs. Brewster High School | FINAL | 2 - 3 | Pawling High School |
| Oct 9, 2026, 6:45 PM | Pawling High School vs. Croton Harmon High School* | FINAL | 0 - 3 | Pawling High School |
| Oct 13, 2026, 6:30 PM | Pawling High School vs. Dobbs Ferry High School* | FINAL | 0 - 3 | Pawling High School |
| Oct 15, 2026, 5:00 PM | Pawling High School vs. Hastings High School* | FINAL | 0 - 3 | Hastings High School |
| Oct 17, 2026, 2:00 PM | Pawling High School vs. Irvington High School* | FINAL | 0 - 3 | Pawling High School |
| Oct 20, 2026, 4:30 PM | Pawling High School vs. Putnam Valley High School* | UPCOMING | - - - | Putnam Valley High School |