| 18/10/25 01:30 | Wellington Olympic0 : 1Auckland City |
| 27/09/25 05:00 | Wellington Phoenix II3 : 5Wellington Olympic |
| 07/09/25 03:00 | Auckland United2 : 4Wellington Olympic |
| 16/08/25 04:00 | Eastern Suburbs AFC- : -Wellington Olympic | ![]() |
| 06/07/25 04:00 | Napier City2 : 3Wellington Olympic |
| 23/11/24 03:00 | Wellington Olympic2 : 3Napier City |
| 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 |
| 07/09/24 09:00 | Wellington Olympic1 : 1Auckland City |
| 27/07/24 04:00 | Wellington Olympic4 : 0Manurewa AFC |
| 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 |
| 24/09/23 02:00 | Manurewa AFCRep.Wellington Olympic |
| 18/03/23 03:30 | Auckland City5 : 3Wellington Olympic |
| 11/03/23 02:00 | Wellington Olympic1 : 1Auckland City |