| All Schools |
| |
| Basketball - Boys |
| 12.07.2018 – Cheverus 58, Windham 48 |
| 12.11.2018 – Portland 59, Windham 46 |
| 12.15.2018 – Bangor 54, Windham 38 |
| 12.18.2018 – Windham 62, Noble 41 |
| 12.21.2018 – Edward Little 50, Windham 28 |
| 12.28.2018 – Bonny Eagle 49, Windham 48 |
| 12.31.2018 – Windham 50, Massabesic 40 |
| 1.05.2019 – Windham 48, Thornton Academy 40 |
| 1.07.2019 – Windham 51, South Portland 49 |
| 1.10.2019 – Windham 48, Sanford 30 |
| 1.15.2019 – Bangor 54, Windham 46 |
| 1.18.2019 – Windham 43, Westbrook 35 |
| 1.21.2019 – Windham 44, Lewiston 37 |
| 1.25.2019 – Deering 51, Windham 43 |
| 1.29.2019 – Oxford Hills 56, Windham 31 |
| 2.01.2019 – Scarborough 64, Windham 41 |
| 2.04.2019 – Gorham 46, Windham 39 |
| 2.07.2019 – Bonny Eagle 38, Windham 33 |
| 2.13.2019 – Edward Little 45, Windham 34 |
| |
| Basketball - Girls |
| 12.07.2018 – Windham 38, Cheverus 36 |
| 12.11.2018 – Windham 55, Portland 46 |
| 12.14.2018 – Windham 44, Bangor 40 |
| 12.18.2018 – Windham 56, Noble 43 |
| 12.21.2018 – Windham 54, Edward Little 40 |
| 12.29.2018 – Windham 46, Bonny Eagle 43 |
| 12.31.2018 – Windham 38, Massabesic 34 |
| 1.08.2019 – South Portland 58, Windham 29 |
| 1.10.2019 – Sanford 49, Windham 43 |
| 1.12.2019 – Scarborough 53, Windham 34 |
| 1.15.2019 – Bangor 41, Windham 37 |
| 1.18.2019 – Windham 45, Westbrook 38 |
| 1.21.2019 – Windham 44, Lewiston 40 |
| 1.25.2019 – Windham 49, Deering 31 |
| 1.29.2019 – Oxford Hills 53, Windham 35 |
| 2.01.2019 – Thornton Academy 46, Windham 45 |
| 2.05.2019 – Gorham 63, Windham 48 |
| 2.07.2019 – Bonny Eagle 46, Windham 34 |
| 2.14.2019 – Deering 41, Windham 26 |
| |
| Field Hockey |
| 9.05.2018 – Windham 1, Massabesic 0 |
| 9.08.2018 – Biddeford 5, Windham 0 |
| 9.11.2018 – Windham 1, South Portland 0 |
| 9.13.2018 – Gorham 4, Windham 0 |
| 9.17.2018 – Thornton Academy 3, Windham 2 |
| 9.19.2018 – Sanford 2, Windham 1 |
| 9.21.2018 – Windham 2, Portland 2 |
| 9.27.2018 – Marshwood 2, Windham 0 |
| 10.04.2018 – Deering 3, Windham 2 |
| 10.05.2018 – Windham 1, Noble 0 |
| 10.09.2018 – Bonny Eagle 3, Windham 0 |
| |
| Football |
| 8.31.2018 – Portland 49, Windham 0 |
| 9.07.2018 – Bangor 14, Windham 0 |
| 9.14.2018 – Edward Little 41, Windham 21 |
| 9.21.2018 – Scarborough 53, Windham 7 |
| 9.28.2018 – Thornton Academy 52, Windham 0 |
| 10.05.2018 – Lewiston 42, Windham 7 |
| 10.13.2018 – Cheverus 48, Windham 6 |
| 10.19.2018 – Oxford Hills/Buckfield 55, Windham 7 |
| |
| Soccer - Boys |
| 9.04.2018 – Windham 2, Bonny Eagle 2 |
| 9.08.2018 – Windham 1, Kennebunk 0 |
| 9.11.2018 – Windham 3, Sanford 0 |
| 9.13.2018 – Windham 1, Westbrook 0 |
| 9.15.2018 – Portland 7, Windham 2 |
| 9.19.2018 – Marshwood 3, Windham 0 |
| 9.20.2018 – Windham 1, Deering 0 |
| 9.26.2018 – South Portland 2, Windham 0 |
| 9.27.2018 – Scarborough 4, Windham 0 |
| 10.02.2018 – Thornton Academy 1, Windham 0 |
| 10.04.2018 – Gorham 5, Windham 0 |
| 10.09.2018 – Windham 4, Biddeford 1 |
| 10.16.2018 – Noble 3, Windham 0 |
| 10.19.2018 – Kennebunk 2, Windham 0 |
| |
| Soccer - Girls |
| 8.30.2018 – Windham 3, South Portland 1 |
| 9.05.2018 – Bonny Eagle 4, Windham 1 |
| 9.08.2018 – Windham 9, Massabesic 1 |
| 9.12.2018 – Windham 1, Deering 0 |
| 9.19.2018 – Windham 4, Portland 3 |
| 9.21.2018 – Noble 1, Windham 0 |
| 9.26.2018 – Windham 3, Thornton Academy 2 |
| 9.29.2018 – Windham 4, Sanford 0 |
| 10.03.2018 – Windham 2, Kennebunk 1 |
| 10.05.2018 – Windham 3, Falmouth 0 |
| 10.10.2018 – Windham 1, Gorham 1 |
| 10.12.2018 – Windham 9, Westbrook 0 |
| 10.16.2018 – Scarborough 3, Windham 0 |
| 10.20.2018 – Windham 1, South Portland 0 |
| 10.24.2018 – Windham 3, Bonny Eagle 0 |
| 10.26.2018 – Scarborough 1, Windham 0 |
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