| All Schools |
| |
| Basketball - Boys |
| 12.07.2019 – Islesboro 45, Greater Portland 31 |
| 12.13.2019 – Gould Academy 54, Islesboro 48 |
| 12.21.2019 – Deer Isle-Stonington 83, Islesboro 34 |
| 1.03.2020 – Rangeley 67, Islesboro 33 |
| 1.04.2020 – Temple 72, Islesboro 32 |
| 1.11.2020 – Rangeley 66, Islesboro 31 |
| 1.14.2020 – Vinalhaven 53, Islesboro 31 |
05:00 PM 1.24.2020 – Deer Isle-Stonington at Islesboro |
11:00 AM 1.25.2020 – Gould Academy at Islesboro |
10:00 AM 1.31.2020 – Vinalhaven at Islesboro |
05:30 PM 2.04.2020 – Islesboro at Greater Portland |
| |
| Basketball - Girls |
| 12.10.2019 – Pine Tree Academy 25, Islesboro 22 |
| 12.19.2019 – North Haven 35, Islesboro 23 |
| 1.03.2020 – Rangeley 80, Islesboro 11 |
| 1.04.2020 – Temple 44, Islesboro 10 |
| 1.09.2020 – North Haven 51, Islesboro 11 |
| 1.11.2020 – Rangeley 73, Islesboro 4 |
| 1.13.2020 – Pine Tree Academy 32, Islesboro 17 |
| 1.22.2020 – North Haven 39, Islesboro 26 |
03:00 PM 1.24.2020 – Islesboro at Kents Hill |
05:00 PM 2.04.2020 – Kents Hill at Islesboro |
05:00 PM 2.06.2020 – Islesboro at Seacoast Christian |
| |
| Soccer - Boys |
| 9.10.2019 – Islesboro 2, Chop Point 0 |
| 9.17.2019 – Islesboro 5, Chop Point 1 |
| 9.20.2019 – Rangeley 3, Islesboro 0 |
| 9.26.2019 – Islesboro 3, Vinalhaven/North Haven 0 |
| 9.27.2019 – Temple 8, Islesboro 3 |
| 10.03.2019 – Islesboro 1, Chop Point 1 |
| 10.04.2019 – Islesboro 3, Seacoast Christian 2 |
| 10.08.2019 – Islesboro 7, Seacoast Christian 2 |
| 10.30.2019 – Pine Tree Academy 5, Islesboro 2 |
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