| All Schools |
| |
| Basketball - Boys |
| 12.06.2019 – Edward Little 58, Windham 44 |
| 12.10.2019 – Portland 55, Windham 54 |
| 12.13.2019 – Bangor 62, Windham 42 |
| 12.20.2019 – Windham 46, Noble 35 |
| 12.23.2019 – Deering 60, Windham 43 |
| 12.28.2019 – Windham 68, Lewiston 42 |
| 1.04.2020 – Windham 35, Oxford Hills 30 |
| 1.07.2020 – Gorham 52, Windham 32 |
| 1.09.2020 – Windham 46, Cheverus 37 |
| 1.11.2020 – Windham 37, Bangor 35 |
| 1.14.2020 – Bonny Eagle 53, Windham 40 |
| 1.17.2020 – Deering 50, Windham 29 |
| 1.24.2020 – Edward Little 55, Windham 35 |
| 1.28.2020 – Windham 18, Portland 16 |
| 1.31.2020 – Lewiston 56, Windham 42 |
| 2.04.2020 – Oxford Hills 50, Windham 42 |
| 2.12.2020 – Windham 51, Lewiston 47 |
| 2.19.2020 – Edward Little 49, Windham 41 |
| |
| Basketball - Girls |
| 12.06.2019 – Windham 41, Edward Little 32 |
| 12.10.2019 – Portland 62, Windham 39 |
| 12.13.2019 – Bangor 47, Windham 39 |
| 12.20.2019 – Noble 68, Windham 57 |
| 12.23.2019 – Windham 54, Deering 18 |
| 1.04.2020 – Oxford Hills 54, Windham 36 |
| 1.06.2020 – Windham 47, Gorham 30 |
| 1.09.2020 – Windham 48, Cheverus 37 |
| 1.11.2020 – Windham 54, Bangor 44 |
| 1.14.2020 – Windham 46, Bonny Eagle 38 |
| 1.17.2020 – Windham 47, Deering 23 |
| 1.24.2020 – Windham 38, Edward Little 34 |
| 1.28.2020 – Portland 52, Windham 41 |
| 1.31.2020 – Windham 53, Lewiston 32 |
| 2.04.2020 – Oxford Hills 76, Windham 57 |
| 2.13.2020 – Windham 49, Cheverus 44 |
| 2.20.2020 – Oxford Hills 54, Windham 31 |
| |
| Field Hockey |
| 9.06.2019 – Windham 3, South Portland 0 |
| 9.10.2019 – Massabesic 4, Windham 1 |
| 9.12.2019 – Windham 3, Falmouth 0 |
| 9.16.2019 – Windham 4, Marshwood 0 |
| 9.18.2019 – Windham 3, Portland/Deering 1 |
| 9.24.2019 – Biddeford 4, Windham 3 |
| 9.26.2019 – Windham 3, Sanford 1 |
| 9.30.2019 – Cheverus 2, Windham 1 |
| 10.02.2019 – Scarborough 2, Windham 0 |
| 10.05.2019 – Bonny Eagle 3, Windham 2 |
| 10.07.2019 – Windham 3, Kennebunk 0 |
| 10.10.2019 – Westbrook 2, Windham 1 |
| 10.19.2019 – Thornton Academy 2, Windham 1 |
| |
| Football |
| 9.06.2019 – Windham 21, Gardiner 20 |
| 9.13.2019 – Windham 35, Hampden Academy 0 |
| 9.20.2019 – Brunswick 27, Windham 14 |
| 9.27.2019 – Windham 42, Brewer 8 |
| 10.04.2019 – Cony 9, Windham 6 |
| 10.11.2019 – Thornton Academy 56, Windham 0 |
| 10.18.2019 – Lawrence 25, Windham 18 |
| 10.25.2019 – Windham 21, Falmouth/Greely 7 |
| 11.01.2019 – Skowhegan 27, Windham 0 |
| |
| Soccer - Boys |
| 9.10.2019 – South Portland 3, Windham 1 |
| 9.13.2019 – Portland 3, Windham 0 |
| 9.17.2019 – Sanford 3, Windham 2 |
| 9.19.2019 – Windham 6, Massabesic 2 |
| 9.21.2019 – Noble 2, Windham 1 |
| 9.24.2019 – Kennebunk 3, Windham 1 |
| 9.26.2019 – Marshwood 3, Windham 0 |
| 10.01.2019 – Falmouth 6, Windham 0 |
| 10.03.2019 – Gorham 3, Windham 0 |
| 10.05.2019 – Cheverus 3, Windham 0 |
| 10.10.2019 – Deering 3, Windham 1 |
| 10.15.2019 – Windham 4, Biddeford 1 |
| 10.19.2019 – Windham 2, Bonny Eagle 1 |
| 10.22.2019 – Westbrook 4, Windham 1 |
| |
| Soccer - Girls |
| 9.10.2019 – Windham 3, South Portland 0 |
| 9.12.2019 – Portland 2, Windham 2 |
| 9.17.2019 – Windham 3, Sanford 0 |
| 9.19.2019 – Windham 6, Massabesic 0 |
| 9.21.2019 – Noble 2, Windham 1 |
| 9.24.2019 – Windham 6, Kennebunk 0 |
| 9.26.2019 – Windham 4, Marshwood 0 |
| 10.01.2019 – Falmouth 2, Windham 2 |
| 10.03.2019 – Gorham 2, Windham 1 |
| 10.08.2019 – Cheverus 1, Windham 0 |
| 10.10.2019 – Windham 4, Deering 0 |
| 10.15.2019 – Windham 5, Biddeford 1 |
| 10.18.2019 – Windham 1, Bonny Eagle 0 |
| 10.22.2019 – Windham 10, Westbrook 0 |
| 10.26.2019 – Windham 5, South Portland 0 |
| 10.29.2019 – Gorham 2, Windham 1 |
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