Head to Head
| New Zealand Central League | 2020/08/29 02:30 | Waterside Karori v Wellington Olympic | W | 3-2 |
| New Zealand Central League | 2020/06/27 03:45 | Wellington Olympic v Waterside Karori | L | 8-1 |
| New Zealand Central League | 2019/08/10 05:50 | Wellington Olympic v Waterside Karori | L | 1-0 |
| New Zealand Central League | 2019/05/18 02:28 | Waterside Karori v Wellington Olympic | W | 4-1 |
| New Zealand Central League | 2018/06/09 05:47 | Wellington Olympic v Waterside Karori | L | 2-1 |
Home History
| New Zealand Central League | 2021/04/24 03:00 | Petone FC v Waterside Karori | L | 3-1 |
| New Zealand Central League | 2021/04/17 03:00 | Waterside Karori v Wairarapa United | D | 2-2 |
| New Zealand Central League | 2021/04/02 02:00 | Waterside Karori v Wainuiomata AFC | W | 2-1 |
| New Zealand Central League | 2021/03/27 01:30 | Miramar Rangers v Waterside Karori | L | 2-1 |
| New Zealand Central League | 2020/09/26 02:30 | Waterside Karori v North Wellington AFC | L | 1-5 |
| New Zealand Central League | 2020/09/19 02:30 | Miramar Rangers v Waterside Karori | L | 8-2 |
| New Zealand Central League | 2020/09/12 02:30 | Waterside Karori v Petone FC | L | 0-2 |
| New Zealand Central League | 2020/09/06 02:33 | Western Suburbs v Waterside Karori | L | 2-0 |
Away History
| New Zealand Central League | 2021/04/16 07:00 | Lower Hutt City v Wellington Olympic | W | 1-2 |
| New Zealand Central League | 2021/04/10 03:00 | Petone FC v Wellington Olympic | W | 1-3 |
| New Zealand Central League | 2021/04/02 02:00 | Wellington Olympic v Wairarapa United | W | 1-0 |
| New Zealand Central League | 2021/03/27 02:00 | North Wellington AFC v Wellington Olympic | D | 3-3 |
| New Zealand Central League | 2020/10/10 01:30 | North Wellington AFC v Wellington Olympic | W | 1-2 |
| New Zealand Central League | 2020/09/26 03:45 | Wellington Olympic v Petone FC | W | 5-0 |
| New Zealand Central League | 2020/09/20 02:30 | Western Suburbs v Wellington Olympic | L | 2-1 |
| New Zealand Central League | 2020/09/05 03:45 | Wellington Olympic v Stop Out | W | 2-0 |