| Day / Date | Opponent | Location | Home / Away | Results / Status | Score |
| Dec 02,2023 | 9:00 AM | Germantown Academy Tournament | Germantown Academy | Away | ||
| Dec 05,2023 | 4:00 PM | Haverford School | Wrestling Gym | Home | Loss | 30 - 39 |
| Dec 09,2023 | 9:00 AM | SCHA Tournament | Springside Chestnut Hill Academy | Away | ||
| Dec 12,2023 | 4:00 PM | Tower Hill | Wrestling Gym | Home | Loss | 34 - 42 |
| Dec 13,2023 | 4:00 PM | Episcopal Academy | Wrestling Gym | Home | Loss | 21 - 45 |
| Jan 06,2024 | 9:00 AM | Westtown Duals | Wrestling Gym | Home | ||
| Jan 13,2024 | 9:15 AM | Church Farm School Tournament | Church Farm School | Away | ||
| Jan 18,2024 | 4:00 PM | George School | Wrestling Gym | Home | Win | 60 - 12 |
| Jan 23,2024 | 4:00 PM | Germantown Friends School | Germantown Friends School | Away | Win | 53 - 27 |
| Jan 27,2024 | 9:00 AM | PAISAA Duals | Wrestling Gym | Home | ||
| Jan 30,2024 | 4:00 PM | Abington Friends School | Wrestling Gym | Home | Win | 60 - 18 |
| Feb 02,2024 | 4:00 PM | Academy of the New Church School | Academy of the New Church School | Away | Win | 54 - 22 |
| Feb 08,2024 | 4:00 PM | FSL Semi-Finals/Championship (vs. Academy of the New Church School) | Wrestling Gym | Home | Win | 60 - 18 |
| Feb 16,2024 | 4:30 PM | PAISWT @ Germantown Academy | Germantown Academy | Away | ||
| Feb 17,2024 | 9:00 AM | PAISWT at Germantown Academy | Germantown Academy | Away | ||
| Feb 23,2024 | 9:00 AM | National Prep at Lehigh University | Lehigh University | Away | ||
| Feb 24,2024 | 9:00 AM | National Prep at Lehigh University | Lehigh University | Away |
Westtown School is a proud member of the Friends Schools League and Pennsylvania Independent School Athletic Association.
