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| Date | Match | Score |
|---|---|---|
| 23.08.2025 | Island Bay United - Wellington Olympic | 0 : 5 |
| 17.05.2025 | Wellington Olympic - Island Bay United | 2 : 0 |
| 03.08.2024 | Wellington Olympic - Island Bay United | 8 : 0 |
| 04.05.2024 | Island Bay United - Wellington Olympic | 1 : 6 |
| Date | Match | Score | Res |
|---|---|---|---|
| 13.12.2025 | Wellington Olympic - Auckland City | 2 - 2 | D |
| 06.12.2025 | Wellington Olympic - Miramar | 2 - 1 | W |
| 30.11.2025 | Auckland United - Wellington Olympic | 0 - 3 | W |
| 21.11.2025 | Wellington Olympic - Christchurch United | 2 - 3 | L |
| 15.11.2025 | Auckland FC 2 - Wellington Olympic | 2 - 1 | L |
| Date | Match | Score | Res |
|---|---|---|---|
| 30.08.2025 | Western Suburbs - Island Bay United | 0 - 0 | D |
| 23.08.2025 | Island Bay United - Wellington Olympic | 0 - 5 | L |
| 09.08.2025 | Petone - Island Bay United | 5 - 0 | L |
| 02.08.2025 | Island Bay United - Miramar | 0 - 3 | L |
| 20.07.2025 | Napier City Rovers - Island Bay United | 4 - 1 | L |