| 07/11/26 02:00 | Wellington Olympic4 : 2Auckland United |
| 31/10/26 02:00 | Miramar Rangers0 : 2Wellington Olympic |
| 17/10/26 04:00 | Wellington Olympic4 : 0Eastern Suburbs AFC |
| 10/10/26 04:00 | Auckland City2 : 2Wellington Olympic |
| 29/08/26 03:45 | Wellington Olympic2 : 1Waterside Karori |
| 13/12/25 06:00 | Wellington Olympic8 : 9Auckland City |
| 06/12/25 02:00 | Wellington Olympic2 : 1Miramar Rangers |
| 22/11/25 00:30 | Wellington Olympic2 : 3Christchurch FC |
| 15/11/25 03:00 | Auckland II2 : 1Wellington Olympic |
| 01/11/25 00:30 | Wellington Olympic1 : 0Western Suburbs |
| 26/10/25 03:00 | Birkenhead United2 : 4Wellington Olympic |
| 18/10/25 01:30 | Wellington Olympic0 : 1Auckland City |
| 12/10/25 03:00 | Coastal Spirit1 : 3Wellington Olympic |
| 04/10/25 01:00 | Wellington Olympic2 : 1Western Springs |
| 27/09/25 05:00 | Wellington Phoenix II3 : 5Wellington Olympic |
| 07/09/25 03:00 | Auckland United2 : 4Wellington Olympic |
| 26/07/25 04:00 | Western Suburbs2 : 3Wellington Olympic |
| 06/07/25 04:00 | Napier City Rovers2 : 3Wellington Olympic |
| 23/11/24 03:00 | Wellington Olympic2 : 3Napier City Rovers |
| 08/11/24 07:00 | Wellington Olympic4 : 1Western Suburbs |
| 02/11/24 01:30 | Wellington Olympic1 : 2Birkenhead United |
| 26/10/24 06:00 | Western Springs2 : 3Wellington Olympic |
| 19/10/24 03:00 | Cashmere Technical2 : 2Wellington Olympic |
| 12/10/24 04:00 | Wellington Olympic4 : 1Eastern Suburbs AFC |
| 05/10/24 04:00 | Wellington Olympic0 : 1Auckland City |
| 28/09/24 04:45 | Coastal Spirit0 : 0Wellington Olympic |
| 07/09/24 09:00 | Wellington Olympic1 : 1Auckland City |
| 18/08/24 03:00 | Coastal Spirit1 : 5Wellington Olympic |
| 27/07/24 04:00 | Wellington Olympic4 : 0Manurewa AFC |
| 06/07/24 04:00 | Wellington Olympic8 : 0Stop Out SC |
| 16/03/24 02:00 | Wellington Olympic3 : 3Auckland City |
| 09/03/24 02:00 | Auckland City1 : 0Wellington Olympic |
| 26/11/23 01:00 | Wellington Olympic2 : 0Auckland City |
| 19/11/23 03:00 | Wellington Olympic4 : 2Wellington Phoenix II |
| 12/11/23 03:00 | Auckland City1 : 3Wellington Olympic |
| 04/11/23 02:00 | Wellington Olympic5 : 2Christchurch FC |
| 28/10/23 01:00 | Wellington Olympic2 : 1Petone FC |
| 21/10/23 04:00 | Auckland United1 : 3Wellington Olympic |
| 14/10/23 04:00 | Wellington Olympic2 : 2Eastern Suburbs AFC |
| 07/10/23 01:00 | Cashmere Technical3 : 3Wellington Olympic |
| 30/09/23 02:00 | Wellington Olympic8 : 1Napier City Rovers |
| 18/03/23 03:30 | Auckland City5 : 3Wellington Olympic |
| 11/03/23 02:00 | Wellington Olympic1 : 1Auckland City |