| Day / Date | Opponent | Location | Home / Away | Results / Status | Score |
| Aug 29,2023 | 3:00 PM | Hun School | Raiford Field | Home | ||
| Aug 30,2023 | 3:00 PM | 3:00-Pennington v Hill 4:00-Pennington v Westtown 5:00-Hill v Westtown | Raiford Field | Home | ||
| Sep 01,2023 | 1:00 PM | Scrimmage v Lansdale Catholic-Ocean City,NJ (vs. Lansdale Catholic High School) | Soccer Complex-150 Tennessee Avenue Ocean City,NJ 08226 | Away | ||
| Sep 06,2023 | 4:00 PM | Springside Chestnut Hill Academy | Raiford Field | Home | Win | 2 - 1 |
| Sep 09,2023 | 2:00 PM | South Kent School | Away | Win | 3 - 2 | |
| Sep 12,2023 | 4:00 PM | Germantown Academy | Germantown Academy | Away | Win | 4 - 0 |
| Sep 16,2023 | 10:00 AM | Westtown Invitational-Westtown v Hoosac School (vs. Hoosac School) | Raiford Field | Home | Win | 3 - 1 |
| Sep 16,2023 | 10:00 AM | Westtown Invitational-Woodstock School 1 v Western Reserve Academy | Balderston Track Field | Home | ||
| Sep 16,2023 | 12:00 PM | Westtown Invitational-Woodstock 2 v Northwood School U17 | Balderston Track Field | Home | ||
| Sep 16,2023 | 12:00 PM | Westtown Invitational-Spire Institute v Northwood School U19 | Raiford Field | Home | ||
| Sep 16,2023 | 2:00 PM | Westtown Invitational-High Mowing School v Lady of Good Counsel | Balderston Track Field | Home | ||
| Sep 16,2023 | 2:00 PM | Westtown Invitational-IHC v Kiski School | Raiford Field | Home | ||
| Sep 17,2023 | 9:00 AM | Mainline High School Jamboree (vs. Woodstock Academy) | USTC | Away | Loss | 0 - 5 |
| Sep 19,2023 | 4:00 PM | Academy of the New Church School | Academy of the New Church School | Away | Win | 6 - 0 |
| Sep 22,2023 | 4:00 PM | Moorestown Friends School | Moorestown Friends School | Away | ||
| Sep 24,2023 | 8:30 AM | NXT Event (Albany) v Worcester (vs. Worcester Academy) | Affirm Sports Complex | Away | Tie | 2 - 2 |
| Sep 26,2023 | 4:00 PM | Abington Friends School | Raiford Field | Home | Win | 8 - 0 |
| Sep 29,2023 | 4:00 PM | Friends Select School | Edgely Field-Fairmount Park | Away | ||
| Sep 30,2023 | 12:00 PM | Haverford School | Away | Loss | 1 - 2 | |
| Oct 03,2023 | 4:00 PM | Germantown Friends School | Germantown Friends School | Away | Win | 5 - 0 |
| Oct 06,2023 | 4:00 PM | Shipley School | Raiford Field | Home | Win | 2 - 0 |
| Oct 07,2023 | 1:00 PM | Caravel Academy | Raiford Field | Home | Win | 3 - 1 |
| Oct 10,2023 | 4:00 PM | Friends Central School | Friends Central School | Away | Win | 1 - 0 |
| Oct 13,2023 | 7:30 PM | George School | Raiford Field | Home | Win | 5 - 0 |
| Oct 17,2023 | 4:00 PM | Barrack Hebrew Academy | Raiford Field | Home | Win | 9 - 0 |
| Oct 25,2023 | 3:00 PM | FSL Semi-Final (vs. Moorestown Friends School) | Raiford Field | Home | Win | 4 - 0 |
| Oct 28,2023 | 1:00 PM | FSL Championship (vs. Shipley School) | Raiford Field | Home | Win | 1 - 0 |
| Nov 07,2023 | 2:30 PM | PAISAA Quarterfinals (vs. Friends Central School) | Raiford Field | Home | Win | 6 - 0 |
| Nov 09,2023 | 3:00 PM | PAISAA Semifinals (vs. Kiski School) | Away | Loss | 0 - 1 |
Westtown School is a proud member of the Friends Schools League and Pennsylvania Independent School Athletic Association.
