| All Schools |
| |
| 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 |
| |
| 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 |
07:00 PM 10.18.2019 – Windham at Lawrence |
07:00 PM 10.25.2019 – Falmouth/Greely at Windham |
| |
| 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 |
06:00 PM 10.15.2019 – Biddeford at Windham |
12:00 PM 10.19.2019 – Windham at Bonny Eagle |
06:00 PM 10.22.2019 – Westbrook at Windham |
| |
| 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 |
06:00 PM 10.15.2019 – Windham at Biddeford |
06:00 PM 10.18.2019 – Bonny Eagle at Windham |
05:30 PM 10.22.2019 – Windham at Westbrook |
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