| 2023-12-16 19:00:00December 16, 2023 | Penn Charter vs Perkiomen Valley | 70 - 74 | PAC | 2023 | Keystone Classic at School of the Future |
| 2021-12-14 13:21:53December 14, 2021 | Germantown Academy vs Penn Charter | 48 - 58 | | | |
| 2019-02-22 18:00:58February 22, 2019 | Shipley School vs Penn Charter (PAISAA semifinal) | 60 - 43 | | 2018 | Germantown Academy |
| 2019-02-14 16:00:00February 14, 2019 | Germantown Academy vs Penn Charter | 69 - 43 | | 2018 | Penn Charter |
| 2019-02-12 16:00:00February 12, 2019 | Agnes Irwin vs Penn Charter | 27 - 65 | | 2018 | Penn Charter |
| 2019-02-08 17:15:00February 8, 2019 | Penn Charter vs Episcopal Academy | 55 - 49 | | 2018 | Episcopal Academy |
| 2019-02-01 17:15:00February 1, 2019 | Penn Charter vs Academy of Notre Dame | 46 - 45 | | 2018 | Academy of Notre Dame |
| 2019-01-29 16:00:00January 29, 2019 | Penn Charter vs Germantown Academy | 44 - 68 | | 2018 | Germantown Academy |
| 2019-01-26 14:30:00January 26, 2019 | St. Basil Academy vs Penn Charter | 32 - 28 | | 2018 | University of the Sciences |
| 2019-01-25 16:00:00January 25, 2019 | Springside-Chestnut Hill vs Penn Charter | 39 - 58 | | 2018 | Penn Charter |
| 2019-01-22 16:00:00January 22, 2019 | Penn Charter vs Agnes Irwin | 62 - 22 | | 2018 | Agnes Irwin |
| 2019-01-18 17:15:00January 18, 2019 | Episcopal Academy vs Penn Charter | 38 - 48 | | 2018 | Penn Charter |
| 2019-01-16 16:00:00January 16, 2019 | Baldwin vs Penn Charter | 35 - 56 | | 2018 | Penn Charter |
| 2019-01-13 13:15:00January 13, 2019 | Wilson vs Penn Charter | 33 - 43 | | 2018 | Play-by-Play Classic (Thomas Jefferson University) |
| 2019-01-11 17:15:00January 11, 2019 | Academy of Notre Dame vs Penn Charter | 59 - 43 | | 2018 | Penn Charter |
| 2019-01-08 16:00:00January 8, 2019 | Penn Charter vs Baldwin | 56 - 34 | | 2018 | Baldwin |
| 2018-12-28 16:30:00December 28, 2018 | Freire Charter vs Penn Charter | 29 - 71 | | 2018 | Penn Charter |
| 2018-12-17 16:00:00December 17, 2018 | Penn Charter vs Springside-Chestnut Hill | 70 - 14 | | 2018 | Springside-Chestnut Hill |
| 2018-12-15 15:30:00December 15, 2018 | George School vs Penn Charter | 29 - 53 | | 2018 | Germantown Academy |
| 2018-12-14 20:47:19December 14, 2018 | Archbishop Ryan vs Penn Charter | 45 - 61 | | | Penn Charter |
| 2018-12-11 19:00:00December 11, 2018 | Penn Charter vs Saint Hubert | 56 - 36 | | 2018 | Saint Hubert |
| 2018-12-08 00:00:00December 8, 2018 | Westtown vs Penn Charter | 51 - 43 | | 2018 | Penn Charter |
| 2018-12-07 13:00:00December 7, 2018 | King’s Christian vs Penn Charter | 36 - 50 | | 2018 | Penn Charter |
| 2018-12-04 17:15:00December 4, 2018 | Abington Friends vs Penn Charter | 43 - 51 | | 2018 | Penn Charter |
| 2018-12-01 18:30:00December 1, 2018 | Penn Charter vs Shipley School | 65 - 52 | | 2018 | Shipley School |
| 2018-11-30 17:30:00November 30, 2018 | Penn Charter vs Westtown | 53 - 61 | | 2018 | Shipley School |
| 2018-11-27 16:00:00November 27, 2018 | Penn Charter vs Friends Central | 48 - 39 | | 2018 | Friends Central |
| 2018-02-17 13:00:55February 17, 2018 | Penn Charter vs Germantown Academy (PAISAA quarterfinals) | 44 - 60 | | 2017 | Germantown Academy |
| 2018-02-09 16:00:00February 9, 2018 | Agnes Irwin vs Penn Charter | 34 - 60 | | 2017 | Agnes Irwin |
| 2018-02-06 16:00:00February 6, 2018 | Penn Charter vs Episcopal Academy | 46 - 51 | | 2017 | Penn Charter |
| 2018-02-01 16:00:00February 1, 2018 | Penn Charter vs Academy of Notre Dame | 45 - 51 | | 2017 | Penn Charter |
| 2018-01-30 16:00:00January 30, 2018 | Baldwin vs Penn Charter | 31 - 28 | | 2017 | Baldwin |
| 2018-01-27 16:30:00January 27, 2018 | Penn Charter vs West Catholic | 35 - 59 | | 2017 | Penn Charter |
| 2018-01-26 16:00:00January 26, 2018 | Penn Charter vs Germantown Academy | 54 - 61 | | 2017 | Penn Charter |
| 2018-01-23 16:00:00January 23, 2018 | Springside-Chestnut Hill vs Penn Charter | 48 - 51 | | 2017 | Springside-Chestnut Hill |
| 2018-01-21 11:30:25January 21, 2018 | Mount Saint Joseph vs Penn Charter | 48 - 37 | | 2017 | Hoops for Hope (University of the Sciences) |
| 2018-01-19 16:00:00January 19, 2018 | Penn Charter vs Agnes Irwin | 60 - 30 | | 2017 | Penn Charter |
| 2018-01-17 17:00:00January 17, 2018 | Penn Charter vs Baldwin | 53 - 31 | | 2017 | Penn Charter |
| 2018-01-16 16:00:00January 16, 2018 | Episcopal Academy vs Penn Charter | 50 - 36 | | 2017 | Episcopal Academy |
| 2018-01-14 13:00:00January 14, 2018 | Ursuline Academy vs Penn Charter | 38 - 48 | | 2017 | Philadelphia University (Play by Play Classic) |
| 2018-01-11 16:30:26January 11, 2018 | Hatboro-Horsham vs Penn Charter | 33 - 43 | | 2017 | Hatboro-Horsham |
| 2018-01-09 17:15:00January 9, 2018 | Academy of Notre Dame vs Penn Charter | 53 - 56 | | 2017 | Academy of Notre Dame |
| 2018-01-03 19:00:00January 3, 2018 | Germantown Academy vs Penn Charter | 55 - 31 | | 2017 | Germantown Academy |
| 2017-12-30 17:45:00December 30, 2017 | Penn Charter vs West Chester Rustin | 47 - 55 | | 2017 | Boardwalk Classic |
| 2017-12-29 17:15:33December 29, 2017 | Holy Spirit vs Penn Charter | 33 - 42 | | 2017 | Boardwalk Classic |
| 2017-12-21 17:30:00December 21, 2017 | Penn Charter vs Saint Hubert | 38 - 33 | | 2017 | Penn Charter |
| 2017-12-19 16:00:00December 19, 2017 | Penn Charter vs Springside-Chestnut Hill | 46 - 50 | | 2017 | Penn Charter |
| 2017-12-16 15:30:00December 16, 2017 | Pennington School vs Penn Charter | 62 - 47 | | 2017 | Germantown Academy |
| 2017-12-15 15:30:00December 15, 2017 | Penn Charter vs Archbishop Ryan | 40 - 47 | | 2017 | Germantown Academy |
| 2017-12-09 17:30:00December 9, 2017 | Penn Charter vs Westtown | 52 - 46 | | 2017 | Penn Charter |
| 2017-12-08 17:00:00December 8, 2017 | King's Christian vs Penn Charter | 19 - 50 | | 2017 | ESF Invitational |
| 2017-12-05 16:00:00December 5, 2017 | Abington Friends vs Penn Charter | 43 - 31 | | 2017 | Abington Friends |
| 2017-12-02 17:00:00December 2, 2017 | Shipley School vs Penn Charter | 47 - 29 | | 2017 | Shipley School |
| 2017-12-01 17:30:00December 1, 2017 | Penn Charter vs Westtown | 38 - 47 | | 2017 | Penn Charter |
| 2017-11-28 16:00:30November 28, 2017 | Friends Central vs Penn Charter | 40 - 57 | | 2017 | |
| 2017-02-14 16:00:00February 14, 2017 | Germantown Academy vs Penn Charter | 70 - 60 | | 2016 | Penn Charter |
| 2017-02-10 16:00:00February 10, 2017 | Springside-Chestnut Hill vs Penn Charter | 46 - 58 | | 2016 | Penn Charter |
| 2017-02-07 16:00:00February 7, 2017 | Agnes Irwin vs Penn Charter | 36 - 45 | | 2016 | Penn Charter |
| 2017-02-03 17:15:00February 3, 2017 | Penn Charter vs Episcopal Academy | 49 - 55 | | 2016 | Episcopal Academy |
| 2017-02-01 16:00:00February 1, 2017 | Baldwin vs Penn Charter | 39 - 52 | | 2016 | Penn Charter |
| 2017-01-29 17:30:00January 29, 2017 | Penn Charter vs Lower Merion | 53 - 43 | | 2016 | Blue Chip Showcase |
| 2017-01-26 17:15:00January 26, 2017 | Penn Charter vs Academy of Notre Dame | 48 - 60 | | 2016 | Academy of Notre Dame |
| 2017-01-23 17:00:00January 23, 2017 | Archbishop Carroll vs Penn Charter | 48 - 32 | | 2016 | Penn Charter |
| 2017-01-20 16:00:00January 20, 2017 | Penn Charter vs Germantown Academy | 33 - 47 | | 2016 | Germantown Academy |
| 2017-01-17 16:00:00January 17, 2017 | Penn Charter vs Springside-Chestnut Hill | 67 - 48 | | 2016 | Springside-Chestnut Hill |
| 2017-01-15 12:00:00January 15, 2017 | Penn Charter vs Sanford School | 43 - 70 | | 2016 | Maggie Lucas Classic |
| 2017-01-13 17:45:00January 13, 2017 | Penn Charter vs Agnes Irwin | 49 - 21 | | 2016 | Agnes Irwin |
| 2017-01-10 16:00:00January 10, 2017 | Episcopal Academy vs Penn Charter | 51 - 33 | | 2016 | Penn Charter |
| 2017-01-08 15:00:00January 8, 2017 | Penn Charter vs Gwynedd Mercy | 32 - 41 | | 2016 | University of the Sciences Showcase |
| 2016-12-30 17:00:00December 30, 2016 | Penn Charter vs Harriton | 66 - 54 | | 2016 | Harriton |
| 2016-12-28 11:00:00December 28, 2016 | Penn Charter vs Archbishop Ryan | 37 - 45 | | 2016 | Boardwalk Classic |
| 2016-12-27 11:00:00December 27, 2016 | Downingtown East vs Penn Charter | 29 - 35 | Daily Local | 2016 | Boardwalk Classic |
| 2016-12-20 15:45:00December 20, 2016 | Olney vs Penn Charter | 32 - 53 | | 2016 | Penn Charter |
| 2016-12-17 15:30:00December 17, 2016 | Mercersburg vs Penn Charter | 24 - 73 | | 2016 | Make-A-Wish Basketball Showcase |
| 2016-12-16 15:30:00December 16, 2016 | Penn Charter vs Archbishop Ryan | 48 - 58 | | 2016 | Make-A-Wish Basketball Showcase |
| 2016-12-14 16:00:00December 14, 2016 | Academy of Notre Dame vs Penn Charter | 33 - 45 | | 2016 | Penn Charter |
| 2016-12-13 16:00:00December 13, 2016 | Penn Charter vs Baldwin | 60 - 34 | | 2016 | Baldwin |
| 2016-12-10 17:30:00December 10, 2016 | Penn Charter vs Archbishop Ryan | 58 - 66 | | 2016 | Archbishop Ryan Tipoff Classic |
| 2016-12-09 16:00:00December 9, 2016 | Penn Charter vs Saint Hubert | 37 - 20 | | 2016 | Archbishop Ryan Tipoff Classic |
| 2016-12-06 15:45:00December 6, 2016 | Abington Friends vs Penn Charter | 41 - 37 | | 2016 | Penn Charter |
| 2016-11-29 17:10:48November 29, 2016 | Penn Charter vs Friends Central | 48 - 27 | | 2016 | |
| 2016-02-20 00:00:58February 20, 2016 | Abington Friends vs Penn Charter | 43 - 36 | Friends School League, Inter-Academic League | 2015 | Penn Charter |
| 2016-02-12 16:00:55February 12, 2016 | Penn Charter vs Germantown Academy | 35 - 72 | Inter-Academic League | 2015 | Germantown Academy |
| 2016-02-09 16:00:00February 9, 2016 | Penn Charter vs Springside-Chestnut Hill | 62 - 55 | Inter-Academic League | 2015 | Springside-Chestnut Hill |
| 2016-02-05 00:00:00February 5, 2016 | Penn Charter vs Agnes Irwin | 52 - 36 | Inter-Academic League | 2015 | Agnes Irwin |
| 2016-02-02 16:00:55February 2, 2016 | Episcopal Academy vs Penn Charter | 59 - 53 | Inter-Academic League | 2015 | Penn Charter |
| 2016-01-30 00:00:00January 30, 2016 | Bishop Shanahan vs Penn Charter | 38 - 56 | Ches-Mont League | 2015 | Blue Chip Showcase |
| 2016-01-27 16:00:00January 27, 2016 | Academy of Notre Dame vs Penn Charter | 41 - 43 | Inter-Academic League | 2015 | Penn Charter |
| 2016-01-22 16:00:00January 22, 2016 | Penn Charter vs Baldwin | 64 - 42 | Inter-Academic League | 2015 | Baldwin |
| 2016-01-19 16:00:26January 19, 2016 | Germantown Academy vs Penn Charter | 54 - 41 | Inter-Academic League | 2015 | Penn Charter |
| 2016-01-17 17:30:00January 17, 2016 | Archbishop Wood vs Penn Charter | 52 - 40 | Catholic League | 2015 | Hoops For Hope Classic (University of Sciences) |
| 2016-01-15 16:00:00January 15, 2016 | Springside-Chestnut Hill vs Penn Charter | 38 - 59 | Inter-Academic League | 2015 | Penn Charter |
| 2016-01-12 16:00:00January 12, 2016 | Agnes Irwin vs Penn Charter | 40 - 54 | Inter-Academic League | 2015 | Penn Charter |
| 2016-01-10 20:30:00January 10, 2016 | Bonner Prendergast vs Penn Charter | 54 - 51 | Catholic League, Inter-Academic League | 2015 | Philadelphia Univ. Tournament |
| 2016-01-08 23:12:33January 8, 2016 | Episcopal Academy vs Penn Charter | 49 - 46 | Inter-Academic League | 2015 | Episcopal Academy |
| 2016-01-05 16:00:00January 5, 2016 | Penn Charter vs Hill School | 57 - 28 | Inter-Academic League, MAPL | 2015 | Hill School |
| 2016-01-03 15:00:02January 3, 2016 | Penn Charter vs Monsignor Scanlan (N.Y.) | 50 - 51 | Inter-Academic League | 2015 | Philly vs. New York Challenge (St. Dominic's, N.Y.) |
| 2015-12-28 00:00:00December 28, 2015 | Haverford vs Penn Charter | 39 - 45 | Central League | 2015 | Wildwood Boardwalk Classic |
| 2015-12-27 17:45:58December 27, 2015 | Penn Charter vs Egg Harbor Township (N.J.) | 56 - 24 | Inter-Academic League | 2015 | Wildwood Boardwalk Classic |
| 2015-12-22 17:15:00December 22, 2015 | Penn Charter vs Academy of Notre Dame | 35 - 53 | Inter-Academic League | 2015 | Academy of Notre Dame |
| 2015-12-19 00:00:55December 19, 2015 | Penn Charter vs McDonogh School | 33 - 52 | Inter-Academic League | 2015 | Germantown Academy |
| 2015-12-18 15:30:00December 18, 2015 | Penn Charter vs Archbishop Ryan | 50 - 37 | Catholic League, Inter-Academic League | 2015 | Germantown Academy |
| 2015-12-15 16:00:00December 15, 2015 | Baldwin vs Penn Charter | 35 - 45 | Inter-Academic League | 2015 | Penn Charter |
| 2015-12-09 16:00:00December 9, 2015 | Penn Charter vs Abington Friends | 49 - 44 | Friends School League, Inter-Academic League | 2015 | Abington Friends |
| 2015-12-08 19:00:00December 8, 2015 | Penn Charter vs Shipley School | 58 - 53 | Friends School League, Inter-Academic League | 2015 | Shipley School |
| 2015-12-05 00:00:17December 5, 2015 | Penn Charter vs Roland Park Country | 50 - 75 | Inter-Academic League | 2015 | Peddie Tip-Off Tournament |
| 2015-12-04 18:00:00December 4, 2015 | Penn Charter vs Peddie School | 62 - 52 | Inter-Academic League, MAPL | 2015 | Peddie Tip-Off Tournament |
| 2015-12-01 16:00:00December 1, 2015 | Friends' Central vs Penn Charter | 59 - 60 | Friends School League, Inter-Academic League | 2015 | Penn Charter |
