| | | | 0-0 (0-0) | Tournament | Milwaukie High School | - | - |
| | | L 0-3 | 0-1 (0-1) | League | Milwaukie, OR | - | - |
| | | L 0-3 | 0-2 (0-2) | League | Hillsboro, OR | - | Watch |
| | | L 0-3 | 0-3 (0-3) | League | Milwaukie, OR | - | - |
| | | W 2-0 | 1-3 (0-3) | Tournament | Milwaukie, OR | - | - |
| | | L 0-2 | 1-4 (0-3) | Tournament | Milwaukie, OR | - | - |
| | | L 0-3 | 1-5 (0-4) | League | Milwaukie, OR | - | - |
| | | L 0-3 | 1-6 (0-5) | League | Milwaukie, OR | - | - |
| | | W 3-1 | 2-6 (1-5) | League | Portland, OR | - | - |
| | | L 0-3 | 2-7 (1-6) | League | Wilsonville, OR | - | Watch |
| | | L 0-3 | 2-8 (1-7) | League | Milwaukie, OR | - | - |
| | | L 0-3 | 2-9 (1-8) | League | Milwaukie, OR | - | Watch |
| | | L 0-3 | 2-10 (1-9) | League | Milwaukie, OR | - | - |
| | | L 0-3 | 2-11 (1-9) | Tournament | Canby High School | - | - |
| | | L 0-3 | 2-12 (1-10) | League | Canby, OR | - | - |
| | | | 2-12 (1-10) | Non League | Hillsboro, OR | - | - |
| | | L 0-3 | 2-13 (1-10) | Non League | Milwaukie, OR | - | - |
| | | L 0-2 | 2-14 (1-10) | Tournament | Seaside, OR | - | - |
| | | W 3-1 | 3-14 (2-10) | League | Milwaukie, OR | - | - |
| | | L 0-3 | 3-15 (2-10) | Non League | Gresham, OR | - | - |
| | | W 3-2 | 4-15 (2-10) | Non League | Milwaukie, OR | - | - |
| | | L 0-3 | 4-16 (2-10) | Non League | Hood River, OR | - | - |