| 2024-02-16 19:00:30February 16, 2024 | (10) Chester vs (7) Phoenixville (District 1 Class 5A First Round) | 42 - 57 | PAC | 2023 | Phoenixville |
| 2023-12-05 18:45:00December 5, 2023 | Chester vs Phoenixville | 58 - 67 | PAC | 2023 | Chester |
| 2022-12-27 18:00:00December 27, 2022 | Chester vs Norristown | 38 - 52 | PAC | 2022 | Conshohocken |
| 2022-12-08 18:45:00December 8, 2022 | Chester vs Phoenixville | 38 - 54 | PAC | 2022 | Phoenixville |
| 2019-12-07 19:00:00December 7, 2019 | Chester vs Phoenixville | 7 - 58 | PAC | 2019 | Phoenixville |
| 2019-02-08 19:00:00February 8, 2019 | Chester vs Wissahickon | 40 - 59 | | 2018 | Wissahickon |
| 2019-02-07 19:00:00February 7, 2019 | Chester vs Academy Park | 44 - 62 | | 2018 | Academy Park |
| 2019-02-05 19:00:00February 5, 2019 | Penn Wood vs Chester | 53 - 42 | | 2018 | Chester |
| 2019-02-02 14:30:00February 2, 2019 | Chester vs Radnor | 33 - 63 | | 2018 | Radnor |
| 2019-01-29 19:00:00January 29, 2019 | Interboro vs Chester | 41 - 37 | | 2018 | Chester |
| 2019-01-24 19:00:00January 24, 2019 | Chichester vs Chester | 26 - 16 | | 2018 | Chester |
| 2019-01-23 14:30:00January 23, 2019 | Great Valley vs Chester | 58 - 33 | | 2018 | Chester |
| 2019-01-22 19:00:00January 22, 2019 | Academy Park vs Chester | 45 - 21 | | 2018 | Chester |
| 2019-01-17 19:00:00January 17, 2019 | Chester vs Penn Wood | 39 - 61 | | 2018 | Penn Wood |
| 2019-01-12 12:00:00January 12, 2019 | Chester vs Harry S. Truman | 58 - 49 | | 2018 | Harry S. Truman |
| 2019-01-08 19:00:00January 8, 2019 | Chester vs Chichester | 45 - 30 | | 2018 | Chichester |
| 2019-01-05 14:30:00January 5, 2019 | Chester vs Conestoga | 24 - 37 | | 2018 | Conestoga |
| 2018-12-28 19:00:27December 28, 2018 | Chester vs Downingtown West | 28 - 29 | | 2018 | Downingtown West |
| 2018-12-14 15:45:00December 14, 2018 | Chester vs Sacred Heart | 28 - 62 | | 2018 | Sacred Heart |
| 2018-12-08 19:00:00December 8, 2018 | Chester vs Phoenixville | 29 - 56 | PAC | 2018 | Phoenixville |
| 2018-12-07 17:00:00December 7, 2018 | Oxford vs Chester | 37 - 28 | | 2018 | Phoenixville |
| 2018-02-08 15:30:00February 8, 2018 | Chester vs Chichester | - | | 2017 | Chester |
| 2018-02-06 23:27:54February 6, 2018 | Penn Wood vs Chester | 55 - 46 | | 2017 | |
| 2018-02-03 15:00:00February 3, 2018 | Chester vs Upper Darby | 44 - 43 | | 2017 | Chester |
| 2018-01-30 19:00:00January 30, 2018 | Chester vs Interboro | 41 - 42 | | 2017 | Chester |
| 2018-01-25 19:00:00January 25, 2018 | Academy Park vs Chester | 70 - 41 | | 2017 | Academy Park |
| 2018-01-23 17:00:00January 23, 2018 | Chichester vs Chester | - | | 2017 | Chichester |
| 2018-01-20 14:30:00January 20, 2018 | Radnor vs Chester | 70 - 56 | | 2017 | Radnor |
| 2018-01-18 19:00:52January 18, 2018 | Penn Wood vs Chester | 49 - 46 | | 2017 | |
| 2018-01-13 14:30:00January 13, 2018 | Great Valley vs Chester | 50 - 25 | | 2017 | Great Valley |
| 2018-01-11 19:00:00January 11, 2018 | Interboro vs Chester | 50 - 35 | | 2017 | Interboro |
| 2018-01-09 17:00:00January 9, 2018 | Chester vs Academy Park | 54 - 67 | | 2017 | Chester |
| 2018-01-03 00:00:36January 3, 2018 | Chester vs Sacred Heart | 35 - 38 | | 2017 | Chester |
| 2018-01-02 19:15:00January 2, 2018 | Sun Valley vs Chester | 40 - 50 | | 2017 | Sun Valley |
| 2017-12-27 23:24:17December 27, 2017 | Nazareth Academy vs Chester | 43 - 32 | | 2017 | |
| 2017-12-21 18:00:00December 21, 2017 | Octorara vs Chester | 12 - 47 | | 2017 | Octorara |
| 2017-12-09 12:00:00December 9, 2017 | North Penn vs Chester | 63 - 9 | | 2017 | North Penn |
| 2017-12-08 18:00:00December 8, 2017 | Chester vs Central Bucks West | 28 - 62 | | 2017 | North Penn |
| 2017-02-08 17:00:00February 8, 2017 | Chester vs Neshaminy | 17 - 45 | | 2016 | Neshaminy |
| 2017-02-07 17:00:00February 7, 2017 | Academy Park vs Chester | 40 - 37 | | 2016 | Chester |
| 2017-02-02 17:00:00February 2, 2017 | Chester vs Chichester | - | | 2016 | Chichester |
| 2017-01-31 19:00:00January 31, 2017 | Interboro vs Chester | 62 - 51 | | 2016 | Chester |
| 2017-01-26 17:00:00January 26, 2017 | Penn Wood vs Chester | 49 - 46 | | 2016 | Chester |
| 2017-01-25 15:45:00January 25, 2017 | Chester vs Sacred Heart | 37 - 48 | | 2016 | Sacred Heart |
| 2017-01-19 19:00:00January 19, 2017 | Chester vs Academy Park | - | | 2016 | Academy Park |
| 2017-01-17 17:00:00January 17, 2017 | Chichester vs Chester | - | | 2016 | Chester |
| 2017-01-16 10:00:00January 16, 2017 | Upper Darby vs Chester | 35 - 50 | | 2016 | Chester |
| 2017-01-12 17:00:00January 12, 2017 | Interboro vs Chester | 37 - 35 | | 2016 | Chester |
| 2017-01-10 19:30:00January 10, 2017 | Chester vs Penn Wood | 45 - 60 | | 2016 | Penn Wood |
| 2017-01-07 15:00:00January 7, 2017 | Chester vs West Catholic | 31 - 73 | | 2016 | West Catholic |
| 2017-01-03 17:00:00January 3, 2017 | Sun Valley vs Chester | 41 - 59 | | 2016 | Chester |
| 2016-12-28 00:00:35December 28, 2016 | Chester vs Nazareth Academy | 46 - 54 | | 2016 | Downingtown West Holiday Tournament |
| 2016-12-27 18:00:00December 27, 2016 | Downingtown West vs Chester | 38 - 26 | Daily Local | 2016 | Holiday Tournament |
| 2016-12-20 17:15:00December 20, 2016 | Chester vs Villa Maria | 41 - 61 | | 2016 | Villa Maria |
| 2016-12-15 17:00:00December 15, 2016 | Wilson vs Chester | 65 - 57 | | 2016 | Chester |
| 2016-12-10 13:30:00December 10, 2016 | Upper Moreland vs Chester | 35 - 42 | | 2016 | Council Rock South Tournament |
| 2016-12-09 19:00:00December 9, 2016 | Chester vs Council Rock South | 21 - 38 | | 2016 | Council Rock South Tip-Off Tournament |
| 2016-02-02 19:00:00February 2, 2016 | Chester vs Academy Park | - | Del-Val | 2015 | Academy Park |
| 2016-01-30 14:30:00January 30, 2016 | Chester vs Villa Maria | 33 - 69 | Catholic Academies, Del-Val | 2015 | Villa Maria |
| 2016-01-26 19:30:00January 26, 2016 | Chester vs Penn Wood | - | Del-Val | 2015 | Penn Wood |
| 2016-01-22 17:00:00January 22, 2016 | Chester vs Chichester | 30 - 47 | Del-Val | 2015 | Chichester |
| 2016-01-16 00:00:06January 16, 2016 | Chester vs Nazareth Academy | 18 - 47 | Catholic Academies, Del-Val | 2015 | Nazareth Academy |
| 2016-01-14 19:30:00January 14, 2016 | Academy Park vs Chester | - | Del-Val | 2015 | Chester |
| 2016-01-09 13:30:00January 9, 2016 | Chester vs Sun Valley | - | Ches-Mont League | 2015 | Sun Valley |
| 2016-01-07 23:52:41January 7, 2016 | Penn Wood vs Chester | 72 - 33 | Del-Val | 2015 | Chester |
| 2016-01-05 23:11:49January 5, 2016 | Chester at Interboro | 33 - 73 | Del-Val | 2015 | Interboro |
| 2016-01-02 13:30:00January 2, 2016 | Reading vs Chester | - | Berks Conference | 2015 | Chester |
| 2015-12-29 00:00:00December 29, 2015 | Strath Haven vs Chester | 60 - 30 | Central League | 2015 | Ridley Holiday Tournament |
| 2015-12-17 18:00:00December 17, 2015 | Chester vs Wilson | 29 - 68 | Berks Conference | 2015 | Wilson |
| 2015-12-15 23:39:37December 15, 2015 | Sacred Heart vs Chester | 47 - 43 | Catholic League, Del-Val | 2015 | Chester |
| 2015-12-11 19:00:00December 11, 2015 | Chester vs Methacton | 16 - 76 | Del-Val, PAC | 2015 | Methacton |
| 2015-12-05 00:00:00December 5, 2015 | Chester vs Great Valley | 23 - 45 | Ches-Mont League | 2015 | Great Valley Tip Off Tournament |
| 2015-12-04 00:00:00December 4, 2015 | Downingtown West vs Chester | 60 - 24 | Ches-Mont League | 2015 | Great Valley Tip Off Tournament |
