| Day / Date | Opponent | Location | Home / Away | Results / Status | Score |
| Sep 08,2023 | 4:00 PM | Lansdale Catholic High School | Lansdale Catholic High School | Away | ||
| Sep 09,2023 | 10:00 AM | FSL Tennis Invitational-CANCELED | Stadium Courts | Home | ||
| Sep 12,2023 | 4:15 PM | Peddie School | Stadium Courts | Home | ||
| Sep 19,2023 | 4:00 PM | Barrack Hebrew Academy | Stadium Courts | Home | Loss | 2 - 3 |
| Sep 22,2023 | 4:00 PM | Academy of the New Church School | Stadium Courts | Home | Win | 4 - 1 |
| Oct 03,2023 | 4:00 PM | Friends Select School | Stadium Courts | Home | Loss | 1 - 3 |
| Oct 05,2023 | 4:00 PM | Friends Central School | Stadium Courts | Home | Loss | 0 - 5 |
| Oct 10,2023 | 4:00 PM | Germantown Friends School | Germantown Friends School | Away | Loss | 0 - 5 |
| Oct 11,2023 | 4:00 PM | Moorestown Friends School | Stadium Courts | Home | Loss | 2 - 3 |
| Oct 13,2023 | 4:00 PM | George School | Stadium Courts | Home | ||
| Oct 16,2023 | 3:45 PM | Delaware County Christian School | DCCC Tennis Courts | Away | ||
| Oct 17,2023 | 4:00 PM | Shipley School | Stadium Courts | Home | Loss | 1 - 4 |
| Oct 18,2023 | 4:00 PM | Abington Friends School | Abington Friends School | Away | Loss | 2 - 3 |
| Oct 23,2023 | 3:00 PM | Quaker Cup Semi-Final (vs. Barrack Hebrew Academy) | Barrack Hebrew Academy | Away | Win | 3 - 2 |
| Oct 24,2023 | 3:00 PM | Quaker Cup Semi-Final@ Abington Friends (vs. Abington Friends School) | Abington Friends School | Away | Win | 4 - 1 |
| Oct 27,2023 | 3:30 PM | Quaker Cup Championship (vs. Friends Select School) | Legacy | Away |
Westtown School is a proud member of the Friends Schools League and Pennsylvania Independent School Athletic Association.
