| Day / Date | Opponent | Location | Home / Away | Results / Status | Score |
| Sep 08,2023 | 4:00 PM | POSTPONED (vs. Baldwin School) | US Cross Country Course | Home | ||
| Sep 13,2023 | 4:00 PM | Shipley School | US Cross Country Course | Home | Loss | 46 - 15 |
| Sep 19,2023 | 4:00 PM | Friends Central School | US Cross Country Course | Home | Loss | 40 - 19 |
| Sep 26,2023 | 4:00 PM | George School | George School | Away | ||
| Oct 03,2023 | 4:30 PM | Germantown Friends School | Belmont Plateau | Away | Loss | 42 - 20 |
| Oct 07,2023 | 3:00 PM | William Tennet Invitational at William Tennet High School | William Tennent High School | Away | ||
| Oct 10,2023 | 4:30 PM | Dock Invitational | Dock Mennonite Academy | Away | ||
| Oct 17,2023 | 3:30 PM | FSL Championship | George School | Away | ||
| Oct 20,2023 | 4:00 PM | Westtown Open Cross Country Race | US Cross Country Course | Home | ||
| Oct 28,2023 | 2:05 PM | PAISAA Championship | Belmont Plateau | Away |
Westtown School is a proud member of the Friends Schools League and Pennsylvania Independent School Athletic Association.
