| Day / Date | Opponent | Location | Home / Away | Results / Status | Score |
| Nov 10,2023 | 4:00 PM | Westtown/Phelps Tournament-SCA v West Nottingham (vs. Covenant College) | Coach Downey Court | Home | Win | 79 - 51 |
| Nov 10,2023 | 6:00 PM | Westtown/Phelps Tournament-Westtown v Convenant Prep | Coach Downey Court | Home | ||
| Nov 10,2023 | 8:00 PM | Westtown/Phelps Tournament-Kiski v Busche Academy | Coach Downey Court | Home | ||
| Nov 11,2023 | 2:00 PM | Westtown/Phelps Tournament-Westtown v Kiski (vs. Kiski School) | Coach Downey Court | Home | Win | 82 - 76 |
| Nov 11,2023 | 4:00 PM | Westtown/Phelps Tournament-Busche Academy v Convenant College | Coach Downey Court | Home | ||
| Nov 11,2023 | 6:00 PM | Westtown/Phelps Tournament-Bridgeport v Compass | Coach Downey Court | Home | ||
| Nov 12,2023 | 12:00 PM | Westtown/Phelps Tournament-Kiski v Convenant College (vs. Busche Academy) | Coach Downey Court | Home | Win | 80 - 63 |
| Nov 12,2023 | 2:00 PM | Westtown/Phelps Tournament-Westtown v Busche Academy | Coach Downey Court | Home | ||
| Nov 12,2023 | 4:00 PM | Westtown/Phelps Tournament-Compass v Olympus | Coach Downey Court | Home | ||
| Nov 17,2023 | 4:30 PM | GAC @ Phelps (vs. West Nottingham Academy) | Phelps School | Away | ||
| Nov 18,2023 | 3:00 PM | GAC @ Phelps (vs. Dynasty (Quebec)) | Phelps School | Away | ||
| Nov 28,2023 | 5:00 PM | Springfield Commonwealth Academy | Coach Downey Court | Home | Loss | 73 - 78 |
| Dec 01,2023 | 5:00 PM | Peddie Tournament vs. Mercersburg (vs. Mercersburg) | Peddie School | Away | Loss | 49 - 60 |
| Dec 02,2023 | 1:00 PM | Peddie Tournament (vs. Kiski School) | Peddie School | Away | Win | 79 - 61 |
| Dec 03,2023 | 10:00 AM | Peddie Tournament (vs. Solebury School) | Peddie School | Away | Win | 92 - 52 |
| Dec 10,2023 | 12:15 PM | Treatment Event @ Widener University vs. MCSCS Basketball | Widener University | Away | ||
| Dec 13,2023 | 5:00 PM | Covenant College | Coach Downey Court | Home | Win | 89 - 77 |
| Dec 15,2023 | 1:00 PM | Phelps School | Phelps School | Away | ||
| Dec 17,2023 | 3:00 PM | Rocktop | Coach Downey Court | Home | ||
| Dec 22,2023 | 4:00 PM | Bullis School | Coach Downey Court | Home | Loss | 53 - 75 |
| Dec 28,2023 | 8:00 PM | Slam Dunk to the Beach (vs. Bishop McNamara) | Cape Henlopen High School | Away | Loss | 57 - 59 |
| Dec 29,2023 | 8:00 PM | Slam Dunk to the Beach (vs. Bella Vista Prep) | Cape Henlopen High School | Away | Win | 50 - 46 |
| Jan 03,2024 | 5:30 PM | Abington Friends School | Coach Downey Court | Home | Win | 71 - 59 |
| Jan 05,2024 | 7:00 PM | Friends Central School | Coach Downey Court | Home | ||
| Jan 06,2024 | 4:30 PM | Community Game | Coach Downey Court | Home | ||
| Jan 06,2024 | 6:00 PM | Olympus Prep | Coach Downey Court | Home | ||
| Jan 12,2024 | 7:00 PM | POSTPONED (vs. Shipley School) | Coach Downey Court | Home | ||
| Jan 17,2024 | 4:00 PM | Barrack Hebrew Academy | Home | Win | 90 - 23 | |
| Jan 20,2024 | 12:00 PM | GAC Tournament-Westtown v Phelps 2 (vs. Phelps School) | Coach Downey Court | Home | Loss | 95 - 86 |
| Jan 20,2024 | 2:00 PM | GAC Tournament-Dyneste v West Nottingham | Coach Downey Court | Home | ||
| Jan 20,2024 | 4:00 PM | GAC Tournament-Our Savior Lutheran v Springfield Commonwealth Academy | Coach Downey Court | Home | ||
| Jan 20,2024 | 6:00 PM | GAC Tournament-Phelps 1 v Olympus | Coach Downey Court | Home | ||
| Jan 21,2024 | 1:00 PM | GAC Tournament Semi-Final Game Dynestie v Olympus Prep | Coach Downey Court | Home | ||
| Jan 21,2024 | 11:00 AM | GAC Tournament Semi-Final Phelps Prep v Our Savior Lutheran | Coach Downey Court | Home | ||
| Jan 21,2024 | 3:00 PM | GAC Tournament Semi-Final Game #7 | Coach Downey Court | Home | ||
| Jan 21,2024 | 5:00 PM | GAC Tournament Semi-Final Game #8 | Coach Downey Court | Home | ||
| Jan 21,2024 | 7:00 PM | GAC Tournament Championship-Our Savior Lutheran v Dynastie | Coach Downey Court | Home | ||
| Jan 23,2024 | 5:30 PM | Germantown Friends School | Germantown Friends School | Away | ||
| Jan 24,2024 | 4:00 PM | Shipley School | Coach Downey Court | Home | ||
| Jan 26,2024 | 7:00 PM | George School | Coach Downey Court | Home | Win | 67 - 49 |
| Jan 28,2024 | 1:00 PM | POSTPONED (vs. Compass Basketball Academy) | Coach Downey Court | Home | ||
| Jan 30,2024 | 5:30 PM | Friends Select School | Friends Select School | Away | ||
| Feb 02,2024 | | FSL 1st Round | TBD | TBD | ||
| Feb 06,2024 | 5:30 PM | FSL Semi-Final v Friends' Central (vs. Friends Central School) | Friends Central School | Away | Loss | 59 - 62 |
| Feb 16,2024 | 4:00 PM | PAISAA 1st Round (vs. Springside Chestnut Hill Academy) | Springside Chestnut Hill Academy | Away | ||
| Feb 20,2024 | 6:30 PM | PAISAA Quarterfinals (vs. Penn Charter) | Penn Charter | Away | Win | 70 - 65 |
| Feb 23,2024 | 5:00 PM | PAISAA Semi-Final (vs. Perkiomen School) | Perkiomen School | Away |
Westtown School is a proud member of the Friends Schools League and Pennsylvania Independent School Athletic Association.
