| All Schools |
| |
| Football |
| 9.01.2023 – Portland 35, Thornton Academy 28 |
| 9.08.2023 – Portland 40, Edward Little 6 |
| 9.15.2023 – Portland 47, Lewiston 6 |
| 9.22.2023 – Portland 2, Falmouth 0 |
| 9.29.2023 – Portland 35, Windham 7 |
| 10.07.2023 – Portland 41, Noble 7 |
| 10.13.2023 – Portland 41, Scarborough 0 |
| 10.31.2023 – Portland 34, South Portland 6 |
| 11.06.2023 – Portland 32, Lewiston 6 |
6 pm 11.06.2023 – Lewiston at Portland |
7 pm 11.11.2023 – Oxford Hills at Portland |
| 11.11.2023 – Portland 29, Oxford Hills 22 |
11 am 11.18.2023 – Thornton Academy at Portland |
| |
| Soccer - Boys |
| 9.01.2023 – Portland 1, Gorham 1 |
| 9.05.2023 – Portland 3, Marshwood 0 |
| 9.07.2023 – Portland 4, Noble 0 |
| 9.12.2023 – Portland 2, Falmouth 0 |
| 9.14.2023 – Portland 4, Sanford 0 |
| 9.19.2023 – Portland 6, Thornton Academy 0 |
| 9.21.2023 – Portland 5, Westbrook 0 |
| 9.26.2023 – Portland 3, Scarborough 0 |
| 9.30.2023 – Kennebunk 1, Portland 0 |
| 10.03.2023 – Portland 2, Biddeford 0 |
| 10.05.2023 – Portland 6, Bonny Eagle 2 |
| 10.09.2023 – Portland 11, Massabesic 0 |
| 10.12.2023 – Deering 3, Portland 1 |
| 10.17.2023 – Portland 2, Marshwood 0 |
| 10.25.2023 – Portland 1, Scarborough 0 |
| 11.02.2023 – Portland 1, Windham 0 |
| 11.07.2023 – Deering 1, Portland 0 |
| |
| Soccer - Girls |
| 8.31.2023 – Thornton Academy 3, Portland 1 |
| 9.06.2023 – Marshwood 6, Portland 1 |
| 9.09.2023 – Windham 6, Portland 0 |
| 9.13.2023 – Portland 4, Massabesic 0 |
| 9.15.2023 – Cheverus 4, Portland 0 |
| 9.22.2023 – Deering 1, Portland 0 |
| 9.26.2023 – Portland 5, Biddeford 3 |
| 9.29.2023 – Portland 2, Kennebunk 1 |
| 10.02.2023 – Scarborough 6, Portland 0 |
| 10.05.2023 – Portland 4, Gorham 4 |
| 10.06.2023 – Noble 4, Portland 2 |
| 10.10.2023 – Portland 5, Westbrook 1 |
| 10.13.2023 – Portland 1, South Portland 0 |
| 10.16.2023 – Sanford 2, Portland 1 |
| 10.20.2023 – Falmouth 2, Portland 0 |
